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4041552Optimizing conditions for the Ugi reaction (MW36-2 to MW36-5)
Experiments
profiles.google.com-micha.wolfleMichael Wolfle still an oil - crude product 295 mg orange-brown high viscous oil - column chromatography (silica gel, EA 100%) [b]Result:[/b] Product [b]MW36-2[/b]: 241 mg (640 µmol, 84%) [url=http://www.ourexperiment.org/data/250.html]1H NMR[/url]: traces of solvent (ethyl acetate) [b]MW36-3:[/b] Additionally added p-toluenesulfonic acid (6.6 mg, 38 µmol, 0.05 eq.) as a Bronstedt acid, stirred for 22 h at room temperature Work-up: oil [b]Result:[/b] - crude yield: 194 mg (493 µmol, 65%) orange-brown oil [data=text]256[/data]: product in high purity – no visible impurities, no further purification needed; traces of solvent (ethyl acetate) [b]MW36-4:[/b] Additionally added zinc triflate (12.6 mg, 38 µmol, 0.05 eq.) as a Lewis acid, stirred for 22 h at room temperature Work-up: oil [b]Result:[/b] Crude yield: 264 mg (671 µmol, 88%) orange-brown oil [data=text]258[/data]: product in high purity – small impurities, no further purification needed; traces of solvent (ethyl acetate) [b]MW36-5:[/b] 2 eq. of paraformaldehyde used, stirred for 22 h at room temperature Work-up: oil [b]Result:[/b] Crude yield: 227 mg (577 µmol, 76%) orange-brown oil [data=text]260[/data]: product in high purity – no visible impurities, no further purification needed; traces of solvent (ethyl acetate) -> Yield improved by heating the reaction, addition of a Lewis-acid and superstoichiometic amount of paraformaldehyde (see [url=http://www.ourexperiment.org/racemic_pzq/321][b]MW36-1[/b][/url]; yield 57%)]]> MW36-1)

Reaction Scheme


Table1 corrected



Hazard and Risk Assessment:
Reaction Class: 2
Hazards: T Toxic, X Irritant, C Corrosive
Risk rating: U = Unlikely

Start time: 2:32 PM 24/06/2010
End time (MW36-2): 9:30 PM 24/06/2010
End time (MW36-3 - 5): 12:45 PM 25/06/2010

General procedure:
To a mixture of paraformaldehyde (22.9 mg/45.8 mg, 762 µmol/1.52 mmol, 1.0/2.0 eq.), 2,2-dimethoxyethylamine (80.1 mg, 762 µmol, 1.0 eq.), cyclohexanecarboxylic acid (97.7 mg, 762 µmol, 1.0 eq.) and optional p-toluenesulfonic acid (6.6 mg, 38 µmol, 0.05 eq.) or zinc triflate (12.6 mg, 38 µmol, 0.05 eq.) in methanol (1 mL) was added slowly 2-phenylethyl isocyanide MW34 (100 mg, 762 µmol, 105 µL 1.0 eq.) and stirred at room temperature or 60°C, respectively.

Work-up: quenched with water, extraction with ethyl acetate, organic layer washed with 1 N HCl, sat. NaCO3 solution and brine, dried over MgSO4, concentrated.

TLC (EA, 100%, stain: Ceric ammonium molybdate, Rf = 0.45)
TLC1
TLC2 MW34_2 + MW40.JPG


MW36-2:
Heated to 60°C, after 7 h complete conversion of the starting material (TLC, EA 100%)

Work-up: added water -> still an oil
- crude product 295 mg orange-brown high viscous oil
- column chromatography (silica gel, EA 100%)
Result:
Product MW36-2: 241 mg (640 µmol, 84%)
1H NMR: traces of solvent (ethyl acetate)

MW36-3:
Additionally added p-toluenesulfonic acid (6.6 mg, 38 µmol, 0.05 eq.) as a Bronstedt acid, stirred for 22 h at room temperature
Work-up: oil
Result:
- crude yield: 194 mg (493 µmol, 65%) orange-brown oil
Data: 1H_NMR MW36-3: product in high purity – no visible impurities, no further purification needed; traces of solvent (ethyl acetate)

MW36-4:
Additionally added zinc triflate (12.6 mg, 38 µmol, 0.05 eq.) as a Lewis acid, stirred for 22 h at room temperature
Work-up: oil
Result:
Crude yield: 264 mg (671 µmol, 88%) orange-brown oil
Data: 1H_NMR MW36-4: product in high purity – small impurities, no further purification needed; traces of solvent (ethyl acetate)

MW36-5:
2 eq. of paraformaldehyde used, stirred for 22 h at room temperature
Work-up: oil
Result:
Crude yield: 227 mg (577 µmol, 76%) orange-brown oil
Data: 1H_NMR MW36-5: product in high purity – no visible impurities, no further purification needed; traces of solvent (ethyl acetate)


-> Yield improved by heating the reaction, addition of a Lewis-acid and superstoichiometic amount of paraformaldehyde (see MW36-1; yield 57%)
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]]>2010-06-25T09:05:59+01:002011-02-07T07:33:00+00:0067a518b7ce88c3984fb127a806afa48c3https://www.ourexperiment.org/data/242.xmlhttps://www.ourexperiment.org/data/244.xmlhttps://www.ourexperiment.org/data/246.xmlhttps://www.ourexperiment.org/data/248.xmlhttps://www.ourexperiment.org/data/250.xmlhttps://www.ourexperiment.org/data/252.xmlhttps://www.ourexperiment.org/data/254.xmlhttps://www.ourexperiment.org/data/256.xmlhttps://www.ourexperiment.org/data/258.xmlhttps://www.ourexperiment.org/data/260.xmlhttp://www.ourexperiment.org/uri/46https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.htmlhttps://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.htmlhttps://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xmlhttps://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.pnghttps://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=404https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=405https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=406https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=407https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=408https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=409https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=410https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=411https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=412https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=413https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=414https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=415https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=416https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=417https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=422https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=423https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=424https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=425https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=426https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=427https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=428https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=1552https://www.ourexperiment.org/racemic_pzq/404/Optimizing_conditions_for_the_Ugi_reaction_MW362_to_MW365.xml?revision=722311Re: Optimizing conditions for the Ugi reaction (MW36-X)ErrorRe: Optimizing conditions for the Ugi reaction (MW36-X)Michael, is this MW36 or MW34? The title/table/text don't match. Also, Jean-Claude raises a question about the NMR correspondence with the literature: http://ff.im/mHiUFMichael, is this MW36 or MW34? The title/table/text don't match. Also, Jean-Claude raises a question about the NMR correspondence with the literature: <a href="http://ff.im/mHiUF">http://ff.im/mHiUF</a>2010-06-27T00:17:50+01:0012Re: Optimizing conditions for the Ugi reaction (MW36-X)ErrorRe: Optimizing conditions for the Ugi reaction (MW36-X)Oh indeed, it should be the reaction number MW36, not MW34. I mixed it when I was using a previous template of the starting material - Thanks.Oh indeed, it should be the reaction number MW36, not MW34. I mixed it when I was using a previous template of the starting material - Thanks.2010-06-28T02:34:47+01:00
4047223Optimizing conditions for the Ugi reaction (MW36-2 to MW36-5)
Experiments
profiles.google.com-micha.wolfleMichael Wolfle still an oil - crude product 295 mg orange-brown high viscous oil - column chromatography (silica gel, EA 100%) [b]Result:[/b] Product [b]MW36-2[/b]: 241 mg (640 µmol, 84%) [url=http://www.ourexperiment.org/data/250.html]1H NMR[/url]: traces of solvent (ethyl acetate) [b]MW36-3:[/b] Additionally added p-toluenesulfonic acid (6.6 mg, 38 µmol, 0.05 eq.) as a Bronstedt acid, stirred for 22 h at room temperature Work-up: oil [b]Result:[/b] - crude yield: 194 mg (493 µmol, 65%) orange-brown oil [data=text]256[/data]: product in high purity – no visible impurities, no further purification needed; traces of solvent (ethyl acetate) [b]MW36-4:[/b] Additionally added zinc triflate (12.6 mg, 38 µmol, 0.05 eq.) as a Lewis acid, stirred for 22 h at room temperature Work-up: oil [b]Result:[/b] Crude yield: 264 mg (671 µmol, 88%) orange-brown oil [data=text]258[/data]: product in high purity – small impurities, no further purification needed; traces of solvent (ethyl acetate) [b]MW36-5:[/b] 2 eq. of paraformaldehyde used, stirred for 22 h at room temperature Work-up: oil [b]Result:[/b] Crude yield: 227 mg (577 µmol, 76%) orange-brown oil [data=text]260[/data]: product in high purity – no visible impurities, no further purification needed; traces of solvent (ethyl acetate) -> Yield improved by heating the reaction, addition of a Lewis-acid and superstoichiometic amount of paraformaldehyde (see [url=http://www.ourexperiment.org/racemic_pzq/321][b]MW36-1[/b][/url]; yield 57%)]]> MW36-1)

Reaction Scheme


Table1 corrected



Hazard and Risk Assessment:
Reaction Class: 2
Hazards: T Toxic, X Irritant, C Corrosive
Risk rating: U = Unlikely

Start time: 2:32 PM 24/06/2010
End time (MW36-2): 9:30 PM 24/06/2010
End time (MW36-3 - 5): 12:45 PM 25/06/2010

General procedure:
To a mixture of paraformaldehyde (22.9 mg/45.8 mg, 762 µmol/1.52 mmol, 1.0/2.0 eq.), 2,2-dimethoxyethylamine (80.1 mg, 762 µmol, 1.0 eq.), cyclohexanecarboxylic acid (97.7 mg, 762 µmol, 1.0 eq.) and optional p-toluenesulfonic acid (6.6 mg, 38 µmol, 0.05 eq.) or zinc triflate (12.6 mg, 38 µmol, 0.05 eq.) in methanol (1 mL) was added slowly 2-phenylethyl isocyanide MW34 (100 mg, 762 µmol, 105 µL 1.0 eq.) and stirred at room temperature or 60°C, respectively.

Work-up: quenched with water, extraction with ethyl acetate, organic layer washed with 1 N HCl, sat. NaCO3 solution and brine, dried over MgSO4, concentrated.

TLC (EA, 100%, stain: Ceric ammonium molybdate, Rf = 0.45)
TLC1
TLC2 MW34_2 + MW40.JPG


MW36-2:
Heated to 60°C, after 7 h complete conversion of the starting material (TLC, EA 100%)

Work-up: added water -> still an oil
- crude product 295 mg orange-brown high viscous oil
- column chromatography (silica gel, EA 100%)
Result:
Product MW36-2: 241 mg (640 µmol, 84%)
1H NMR: traces of solvent (ethyl acetate)

MW36-3:
Additionally added p-toluenesulfonic acid (6.6 mg, 38 µmol, 0.05 eq.) as a Bronstedt acid, stirred for 22 h at room temperature
Work-up: oil
Result:
- crude yield: 194 mg (493 µmol, 65%) orange-brown oil
Data: 1H_NMR MW36-3: product in high purity – no visible impurities, no further purification needed; traces of solvent (ethyl acetate)

MW36-4:
Additionally added zinc triflate (12.6 mg, 38 µmol, 0.05 eq.) as a Lewis acid, stirred for 22 h at room temperature
Work-up: oil
Result:
Crude yield: 264 mg (671 µmol, 88%) orange-brown oil
Data: 1H_NMR MW36-4: product in high purity – small impurities, no further purification needed; traces of solvent (ethyl acetate)

MW36-5:
2 eq. of paraformaldehyde used, stirred for 22 h at room temperature
Work-up: oil
Result:
Crude yield: 227 mg (577 µmol, 76%) orange-brown oil
Data: 1H_NMR MW36-5: product in high purity – no visible impurities, no further purification needed; traces of solvent (ethyl acetate)


-> Yield improved by heating the reaction, addition of a Lewis-acid and superstoichiometic amount of paraformaldehyde (see MW36-1; yield 57%)
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