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23397384Preparation of the dimethoxy Ugi-intermediate using 2,2-Diethoxyethylamine
Experiments
plus.google.com-113014781212630252105Murray Robertson

Hazard and Risk Assessment:[data]1386[/data]

ProcedureTo a mixture of formaldehyde solution (0.21 ml, 2.33 mmol), 2,2-dimethoxyethylamine (0.34 mL, 2.33 mmol) and cyclohexanecarboxylic acid (300 mg, 2.33 mmol) in methanol (1.5 mL) was added slowly 2-(3,4-Dimethoxyphenyl)ethyl isocyanide MNR4-1 (0.56 mL, 2.33 mmol) and stirred at room temperature for 24 h. EtOAc (5 mL) was then added to the reaction and was washed with 1 M HCl (5 mL), sat. NaCO3 solution (5mL) and brine (5 mL), dried over MgSO4, filtered and concentrated.

A highly viscous orange-brown oil was obtained which was purified by column chromatography (silica gel, EtOAc/Hexane 75-100%) to give the product as clear oil 0.941 g, 2.0 mmol, 63%

* formaldehyde solution was used rather than paraformaldehyde. The exact concentration of the solution was unclear. Also the wrong density was used for MNR4-1 was used as has not been determined. Therefore, two areas where stoichiometry errors have more than likely occurred.

Column frac 5-14 clear oil

LCMS [data]1486[/data] observed peaks rt 19.917-20.333 419 hemiaminal+H 487 M+H

rt 20.683-21.317 415 unknown C22H28N2O5+H

similar to LCMS of MW40 where hemiaminal+H (405) and M+Na (459) [data]1488[/data]

1H NMR MNR8-1contains the same impurities as MW40

LRMS [data]5343[/data]

HRMS [data]5345[/data]

Lab book page complete, MNR

]]>

Hazard and Risk Assessment:

HIRAC MNR8.pdf

ProcedureTo a mixture of formaldehyde solution (0.21 ml, 2.33 mmol), 2,2-dimethoxyethylamine (0.34 mL, 2.33 mmol) and cyclohexanecarboxylic acid (300 mg, 2.33 mmol) in methanol (1.5 mL) was added slowly 2-(3,4-Dimethoxyphenyl)ethyl isocyanide MNR4-1 (0.56 mL, 2.33 mmol) and stirred at room temperature for 24 h. EtOAc (5 mL) was then added to the reaction and was washed with 1 M HCl (5 mL), sat. NaCO3 solution (5mL) and brine (5 mL), dried over MgSO4, filtered and concentrated.

A highly viscous orange-brown oil was obtained which was purified by column chromatography (silica gel, EtOAc/Hexane 75-100%) to give the product as clear oil 0.941 g, 2.0 mmol, 63%

* formaldehyde solution was used rather than paraformaldehyde. The exact concentration of the solution was unclear. Also the wrong density was used for MNR4-1 was used as has not been determined. Therefore, two areas where stoichiometry errors have more than likely occurred.

Column frac 5-14 clear oil

LCMS

LCMS_mnr8-1.pdf
observed peaks rt 19.917-20.333 419 hemiaminal+H 487 M+H

rt 20.683-21.317 415 unknown C22H28N2O5+H

similar to LCMS of MW40 where hemiaminal+H (405) and M+Na (459)

LCMS MW40-1 starting material for MW56-3.pdf

1H NMR MNR8-1contains the same impurities as MW40

LRMS 

7d LRMS MNR8-1 dont include.jpg

HRMS 

7d HRMS MNR8-1.jpg

Lab book page complete, MNR

Linked Entries
This entry is linked by:
]]>2011-09-13T08:31:11+01:002016-01-26T19:05:54+00:006https://www.ourexperiment.org/data/1382.xmlhttps://www.ourexperiment.org/data/1384.xmlhttps://www.ourexperiment.org/data/1386.xmlhttps://www.ourexperiment.org/data/1486.xmlhttps://www.ourexperiment.org/data/1488.xmlhttps://www.ourexperiment.org/data/1901.xmlhttps://www.ourexperiment.org/data/1903.xmlhttps://www.ourexperiment.org/data/5343.xmlhttps://www.ourexperiment.org/data/5345.xmlhttp://www.ourexperiment.org/uri/166https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.htmlhttps://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.htmlhttps://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xmlhttps://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.pnghttps://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2339https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2340https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2341https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2342https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2343https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2344https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2345https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2346https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2391https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2520https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2521https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2522https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2523https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=3031https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=3032https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=3033https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=7384https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=7084https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=7373https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=-1
23397373Preparation of the dimethoxy Ugi-intermediate using 2,2-Diethoxyethylamine
Experiments
plus.google.com-113014781212630252105Murray Robertson

Hazard and Risk Assessment:[data]1386[/data]

ProcedureTo a mixture of formaldehyde solution (0.21 ml, 2.33 mmol), 2,2-dimethoxyethylamine (0.34 mL, 2.33 mmol) and cyclohexanecarboxylic acid (300 mg, 2.33 mmol) in methanol (1.5 mL) was added slowly 2-(3,4-Dimethoxyphenyl)ethyl isocyanide MNR4-1 (0.56 mL, 2.33 mmol) and stirred at room temperature for 24 h. EtOAc (5 mL) was then added to the reaction and was washed with 1 M HCl (5 mL), sat. NaCO3 solution (5mL) and brine (5 mL), dried over MgSO4, filtered and concentrated.

A highly viscous orange-brown oil was obtained which was purified by column chromatography (silica gel, EtOAc/Hexane 75-100%) to give the product as clear oil 0.941 g, 2.0 mmol, 63%

* formaldehyde solution was used rather than paraformaldehyde. The exact concentration of the solution was unclear. Also the wrong density was used for MNR4-1 was used as has not been determined. Therefore, two areas where stoichiometry errors have more than likely occurred.

Column frac 5-14 clear oil

LCMS [data]1486[/data] observed peaks rt 19.917-20.333 419 hemiaminal+H 487 M+H

rt 20.683-21.317 415 unknown C22H28N2O5+H

similar to LCMS of MW40 where hemiaminal+H (405) and M+Na (459) [data]1488[/data]

1H NMR MNR8-1contains the same impurities as MW40

LRMS [data]5343[/data]

HRMS [data]5345[/data]

Lab book page complete, MNR

]]>

Hazard and Risk Assessment:

HIRAC MNR8.pdf

ProcedureTo a mixture of formaldehyde solution (0.21 ml, 2.33 mmol), 2,2-dimethoxyethylamine (0.34 mL, 2.33 mmol) and cyclohexanecarboxylic acid (300 mg, 2.33 mmol) in methanol (1.5 mL) was added slowly 2-(3,4-Dimethoxyphenyl)ethyl isocyanide MNR4-1 (0.56 mL, 2.33 mmol) and stirred at room temperature for 24 h. EtOAc (5 mL) was then added to the reaction and was washed with 1 M HCl (5 mL), sat. NaCO3 solution (5mL) and brine (5 mL), dried over MgSO4, filtered and concentrated.

A highly viscous orange-brown oil was obtained which was purified by column chromatography (silica gel, EtOAc/Hexane 75-100%) to give the product as clear oil 0.941 g, 2.0 mmol, 63%

* formaldehyde solution was used rather than paraformaldehyde. The exact concentration of the solution was unclear. Also the wrong density was used for MNR4-1 was used as has not been determined. Therefore, two areas where stoichiometry errors have more than likely occurred.

Column frac 5-14 clear oil

LCMS

LCMS_mnr8-1.pdf
observed peaks rt 19.917-20.333 419 hemiaminal+H 487 M+H

rt 20.683-21.317 415 unknown C22H28N2O5+H

similar to LCMS of MW40 where hemiaminal+H (405) and M+Na (459)

LCMS MW40-1 starting material for MW56-3.pdf

1H NMR MNR8-1contains the same impurities as MW40

LRMS 

7d LRMS MNR8-1 dont include.jpg

HRMS 

7d HRMS MNR8-1.jpg

Lab book page complete, MNR

Linked Entries
This entry is linked by:
]]>2011-09-13T08:31:11+01:002016-01-19T13:15:57+00:00637e8e5c6a42f6bd958691234fa02cf12https://www.ourexperiment.org/data/1382.xmlhttps://www.ourexperiment.org/data/1384.xmlhttps://www.ourexperiment.org/data/1386.xmlhttps://www.ourexperiment.org/data/1486.xmlhttps://www.ourexperiment.org/data/1488.xmlhttps://www.ourexperiment.org/data/1901.xmlhttps://www.ourexperiment.org/data/1903.xmlhttps://www.ourexperiment.org/data/5343.xmlhttps://www.ourexperiment.org/data/5345.xmlhttp://www.ourexperiment.org/uri/166https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.htmlhttps://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.htmlhttps://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xmlhttps://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.pnghttps://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2339https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2340https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2341https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2342https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2343https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2344https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2345https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2346https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2391https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2520https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2521https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2522https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=2523https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=3031https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=3032https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=3033https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=7384https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=7084https://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.xml?revision=7373