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3381585Scale-up - Preparation of 2-Phenylethyl isocyanide (MW34-2)
Experiments
profiles.google.com-micha.wolfleMichael Wolfle not engough NaOH? - 2 equivalents used instead of 4 eq. in the previous trial]]>Ugi reaction – upscaling of reaction MW34-1

Reaction Scheme1


Table1


Start time: 10:45 AM 16/06/2010
End time: 9:50 AM 17/06/2010

To a mixture of phenethylamine (5.00 g, 41.3 mmol), benzyltriethylammonium chloride (TEBACl) (470 mg, 2.06 µmol, 5 mol%) and NaOH (3.30 g, 61.9 mmol, 2 eq.) in CH2Cl2 (30 mL) was added chloroform (7.39 g, 5.0 mL, 61.9 mmol, 1.5 eq.) and heated to reflux.
- after 12 h the solution was cooled to room temperature and stirred vigorously for another 12 h.
TLC (hexane:EA, 4:1, stain: KMnO4): some remaining starting material

Work-up: quenched with water, extracted with DCM, washed with 1 N aq. HCl-solution, dried over magnesium sulfate, concentrated.
- dark brown oil, crude yield: 3.32 g
- purification by column chromatography (silica gel, hexane/EA, 6:1, stain: KMnO4), Rf = 0.28

Result:
Product MW34-2: 1.72 g (13.1 mmol, 32%) brown liquid; yield reference: 60% [1]

-> not engough NaOH? - 2 equivalents used instead of 4 eq. in the previous trial
Linked Posts
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]]>2010-06-16T06:39:13+01:002011-02-10T04:11:16+00:006c933de8e3a8d4c1e86fd184dff665027https://www.ourexperiment.org/data/196.xmlhttps://www.ourexperiment.org/data/198.xmlhttp://www.ourexperiment.org/uri/41https://www.ourexperiment.org/racemic_pzq/338/Scaleup__Preparation_of_2Phenylethyl_isocyanide_MW342.htmlhttps://www.ourexperiment.org/racemic_pzq/338/Scaleup__Preparation_of_2Phenylethyl_isocyanide_MW342.htmlhttps://www.ourexperiment.org/racemic_pzq/338/Scaleup__Preparation_of_2Phenylethyl_isocyanide_MW342.xmlhttps://www.ourexperiment.org/racemic_pzq/338/Scaleup__Preparation_of_2Phenylethyl_isocyanide_MW342.pnghttps://www.ourexperiment.org/racemic_pzq/338/Scaleup__Preparation_of_2Phenylethyl_isocyanide_MW342.xml?revision=362https://www.ourexperiment.org/racemic_pzq/338/Scaleup__Preparation_of_2Phenylethyl_isocyanide_MW342.xml?revision=361https://www.ourexperiment.org/racemic_pzq/338/Scaleup__Preparation_of_2Phenylethyl_isocyanide_MW342.xml?revision=338https://www.ourexperiment.org/racemic_pzq/338/Scaleup__Preparation_of_2Phenylethyl_isocyanide_MW342.xml?revision=339https://www.ourexperiment.org/racemic_pzq/338/Scaleup__Preparation_of_2Phenylethyl_isocyanide_MW342.xml?revision=340https://www.ourexperiment.org/racemic_pzq/338/Scaleup__Preparation_of_2Phenylethyl_isocyanide_MW342.xml?revision=341https://www.ourexperiment.org/racemic_pzq/338/Scaleup__Preparation_of_2Phenylethyl_isocyanide_MW342.xml?revision=343https://www.ourexperiment.org/racemic_pzq/338/Scaleup__Preparation_of_2Phenylethyl_isocyanide_MW342.xml?revision=1563https://www.ourexperiment.org/racemic_pzq/338/Scaleup__Preparation_of_2Phenylethyl_isocyanide_MW342.xml?revision=1585https://www.ourexperiment.org/racemic_pzq/338/Scaleup__Preparation_of_2Phenylethyl_isocyanide_MW342.xml?revision=6990
3386990Scale-up - Preparation of 2-Phenylethyl isocyanide (MW34-2)
Experiments
profiles.google.com-micha.wolfleMichael Wolfle not engough NaOH? - 2 equivalents used instead of 4 eq. in the previous trial]]>Ugi reaction – upscaling of reaction MW34-1

Reaction Scheme1


Table1


Start time: 10:45 AM 16/06/2010
End time: 9:50 AM 17/06/2010

To a mixture of phenethylamine (5.00 g, 41.3 mmol), benzyltriethylammonium chloride (TEBACl) (470 mg, 2.06 µmol, 5 mol%) and NaOH (3.30 g, 61.9 mmol, 2 eq.) in CH2Cl2 (30 mL) was added chloroform (7.39 g, 5.0 mL, 61.9 mmol, 1.5 eq.) and heated to reflux.
- after 12 h the solution was cooled to room temperature and stirred vigorously for another 12 h.
TLC (hexane:EA, 4:1, stain: KMnO4): some remaining starting material

Work-up: quenched with water, extracted with DCM, washed with 1 N aq. HCl-solution, dried over magnesium sulfate, concentrated.
- dark brown oil, crude yield: 3.32 g
- purification by column chromatography (silica gel, hexane/EA, 6:1, stain: KMnO4), Rf = 0.28

Result:
Product MW34-2: 1.72 g (13.1 mmol, 32%) brown liquid; yield reference: 60% [1]

-> not engough NaOH? - 2 equivalents used instead of 4 eq. in the previous trial
Linked Entries
This entry is linked by:
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