반응 #656152

반응 방정식

HCl

3-benzyloxy-1-propanol

3-Benzyloxy-1-propanol

DMSO

oxalyl chloride

→

aldehyde

3-Benzyloxy-1-propanal

용매

triethylamine

CH2Cl2

dichloromethane

CH2Cl2

반응 조건

후처리

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITis continued for 15 min
3. 3
   workup.WAITAfter 5 min at this temperature
4. 4
   온도to warm up to room temperature
5. 5
   세척the organic phase is washed with water until neutral
6. 6
   기타Drying
7. 7
   기타(Na2SO4) and evaporation

실험 절차

Under nitrogen, a solution of DMSO (8.4 mL, 118 mmoles) in dry dichloromethane (125 mL) is cooled to -60° C., and oxalyl chloride (5 mL, 59 mmoles) in CH2Cl2 (40 mL) is added slowly. After stirring for 5 min at -50° C., 3-benzyloxy-1-propanol (14), 8.9 g, 53.7 mmoles) in CH2Cl2 (27 mL) is added at -60° C. Stirring is continued for 15 min, then triethylamine (47 mL) is added slowly at -60° C. After 5 min at this temperature, the mixture is allowed to warm up to room temperature. After addition of 0.5N HCl and phase separation, the organic phase is washed with water until neutral. Drying (Na2SO4) and evaporation gives the crude aldehyde as an oil: 10.6 g. Distillation under vacuum gives pure 15: 6.54 g (74%), bp 170° C. (15 mm Hg).

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