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23925505Preparation of the dimethoxy Ugi-intermediate (MNR8-2) using 2,2-Diethoxyethylamine
Experiments
plus.google.com-113014781212630252105Murray Robertson [b]Hazard and Risk Assessment:[/b] As for [url=http://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.html]MNR8-1[/url] [b]Procedure[/b] To a mixture of formaldehyde solution (1.11 ml, 12.55 mmol), 2,2-dimethoxyethylamine (1.82 mL, 12.55 mmol) and cyclohexanecarboxylic acid (1.56 mL, 12.55 mmol) in methanol (10 mL) was added slowly 2-(3,4-Dimethoxyphenyl)ethyl isocyanide MNR4-1 (2.4 g, 12.55 mmol) and stirred at room temperature for 24 h. EtOAc (20 mL) was then added to the reaction and was washed with 1 M HCl (20 mL), sat. NaCO3 solution (20mL) and brine (20 mL), dried over MgSO4, filtered and concentrated. Crude:- 4.994 g as a dark orange oil FCC 2.882 g, 6.20 mmol, 49 % as a clear oil - why such a low yiels and low recovery from the column?? 1H NMR MNR8-2 similar to MNR8-1 [i]Lab book page complete, MNR[/i]]]>


Hazard and Risk Assessment:

As for MNR8-1

Procedure
To a mixture of formaldehyde solution (1.11 ml, 12.55 mmol), 2,2-dimethoxyethylamine (1.82 mL, 12.55 mmol) and cyclohexanecarboxylic acid (1.56 mL, 12.55 mmol) in methanol (10 mL) was added slowly 2-(3,4-Dimethoxyphenyl)ethyl isocyanide MNR4-1 (2.4 g, 12.55 mmol) and stirred at room temperature for 24 h. EtOAc (20 mL) was then added to the reaction and was washed with 1 M HCl (20 mL), sat. NaCO3 solution (20mL) and brine (20 mL), dried over MgSO4, filtered and concentrated.

Crude:- 4.994 g as a dark orange oil

FCC 2.882 g, 6.20 mmol, 49 % as a clear oil - why such a low yiels and low recovery from the column??

1H NMR MNR8-2 similar to MNR8-1

Lab book page complete, MNR
Linked Posts
This post is linked by:
]]>2011-09-27T02:03:37+01:002012-05-02T07:00:11+01:006604f860653285921a9d3ba8eb6a429cahttps://www.ourexperiment.org/data/1416.xmlhttps://www.ourexperiment.org/data/1418.xmlhttps://www.ourexperiment.org/data/1905.xmlhttps://www.ourexperiment.org/data/1907.xmlhttps://www.ourexperiment.org/data/4015.xmlhttps://www.ourexperiment.org/data/4017.xmlhttp://www.ourexperiment.org/uri/16bhttps://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.htmlhttps://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.htmlhttps://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xmlhttps://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.pnghttps://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=2392https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=2393https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=2394https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=2395https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=2413https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=2505https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=2665https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=3034https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=3035https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=3036https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=5503https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=5504https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=5505https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=7308
23927308Preparation of the dimethoxy Ugi-intermediate (MNR8-2) using 2,2-Diethoxyethylamine
Experiments
plus.google.com-113014781212630252105Murray Robertson [b]Hazard and Risk Assessment:[/b] As for [url=http://www.ourexperiment.org/racemic_pzq/2339/Preparation_of_the_dimethoxy_Ugiintermediate_using_22Diethoxyethylamine.html]MNR8-1[/url] [b]Procedure[/b] To a mixture of formaldehyde solution (1.11 ml, 12.55 mmol), 2,2-dimethoxyethylamine (1.82 mL, 12.55 mmol) and cyclohexanecarboxylic acid (1.56 mL, 12.55 mmol) in methanol (10 mL) was added slowly 2-(3,4-Dimethoxyphenyl)ethyl isocyanide MNR4-1 (2.4 g, 12.55 mmol) and stirred at room temperature for 24 h. EtOAc (20 mL) was then added to the reaction and was washed with 1 M HCl (20 mL), sat. NaCO3 solution (20mL) and brine (20 mL), dried over MgSO4, filtered and concentrated. Crude:- 4.994 g as a dark orange oil FCC 2.882 g, 6.20 mmol, 49 % as a clear oil - why such a low yiels and low recovery from the column?? 1H NMR MNR8-2 similar to MNR8-1 [i]Lab book page complete, MNR[/i]]]>


Hazard and Risk Assessment:

As for MNR8-1

Procedure
To a mixture of formaldehyde solution (1.11 ml, 12.55 mmol), 2,2-dimethoxyethylamine (1.82 mL, 12.55 mmol) and cyclohexanecarboxylic acid (1.56 mL, 12.55 mmol) in methanol (10 mL) was added slowly 2-(3,4-Dimethoxyphenyl)ethyl isocyanide MNR4-1 (2.4 g, 12.55 mmol) and stirred at room temperature for 24 h. EtOAc (20 mL) was then added to the reaction and was washed with 1 M HCl (20 mL), sat. NaCO3 solution (20mL) and brine (20 mL), dried over MgSO4, filtered and concentrated.

Crude:- 4.994 g as a dark orange oil

FCC 2.882 g, 6.20 mmol, 49 % as a clear oil - why such a low yiels and low recovery from the column??

1H NMR MNR8-2 similar to MNR8-1

Lab book page complete, MNR
Linked Entries
This entry is linked by:
]]>2011-09-27T02:03:37+01:002015-08-21T05:35:30+01:006https://www.ourexperiment.org/data/1416.xmlhttps://www.ourexperiment.org/data/1418.xmlhttps://www.ourexperiment.org/data/1905.xmlhttps://www.ourexperiment.org/data/1907.xmlhttps://www.ourexperiment.org/data/4015.xmlhttps://www.ourexperiment.org/data/4017.xmlhttp://www.ourexperiment.org/uri/16bhttps://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.htmlhttps://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.htmlhttps://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xmlhttps://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.pnghttps://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=2392https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=2393https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=2394https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=2395https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=2413https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=2505https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=2665https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=3034https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=3035https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=3036https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=5503https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=5504https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=5505https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=7308https://www.ourexperiment.org/racemic_pzq/2392/Preparation_of_the_dimethoxy_Ugiintermediate_MNR82_using_22Diethoxyethylamine.xml?revision=-1