反应 #367276

反应方程式

DIBAL

ester

ethyl 3-[2,5-dimethyl-6-(dimethylphenylsilyl)phenyl]-prop-2-enoate

→

clear oil

3-[2,5-dimethyl-6-(dimethylphenylsilyl)phenyl]prop-2-enol

溶剂

toluene

toluene

反应条件

后处理

1. 1
   温度with slow warming to 0°
2. 2
   温度The reaction was then re-cooled (-40°)
3. 3
   其他quenched with saturated aqueous sodium sulfate
4. 4
   workup.ADDITIONSolid sodium sulfate and celite were added
5. 5
   workup.ADDITIONthe mixture was diluted with MTBE
6. 6
   workup.STIRRINGstirred 10 minutes
7. 7
   过滤filtered
8. 8
   浓缩The filtrate was concentrated

实验过程

A 1M solution of DIBAL in toluene (8.6 ml) was added slowly to the ester product of step (t) above (0.967 g, 2.86 mmol) in 5 ml of toluene at -78°. The reaction was stirred 4 hours with slow warming to 0°. The reaction was then re-cooled (-40°) and quenched with saturated aqueous sodium sulfate. Solid sodium sulfate and celite were added and the mixture was diluted with MTBE, stirred 10 minutes, and then filtered. The filtrate was concentrated to give 0.97 g of a clear oil which was chromatographed on silica gel (230-400 mesh) using a 3"×6.5" column with a 3:1 mixture of hexane and ethyl acetate as the eluent; 602 mg (71%) of refined alcohol product of this step was obtained.

来源