反应 #2647

反应方程式

(-)-acetic acid 4-tert-butyldimethylsilyloxy-cyclopent-2-enyl ester

lithium hydroxide monohydrate

water

→

title compound

收率 92.0%

(+)-cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol

收率 92.0%

溶剂

THF methanol water

反应条件

后处理

1. 1
   workup.ADDITIONdilute
2. 2
   萃取extract with tert-butyl methyl ether
3. 3
   干燥dry over anhydrous magnesium sulfate
4. 4
   过滤filter
5. 5
   浓缩concentrate under vacuum
6. 6
   其他Purify the residue by flash chromatography (silica gel, 20% ethyl acetate/hexane)

实验过程

Dissolve (-)-acetic acid 4-tert-butyldimethylsilyloxy-cyclopent-2-enyl ester (2.3 mmol, prepared in example 10) in THF/methanol/water (2.7/0.9/0.9 mL). Add lithium hydroxide monohydrate (2.5 mmol) with stirring. After stirring for about 3 hours at room temperature, dilute the reaction with water (10 mL) and extract with tert-butyl methyl ether. Combine the organic phases, dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by flash chromatography (silica gel, 20% ethyl acetate/hexane) to provide the title compound (452 mg, 92% yield) [α]20D =+21.8°, (c=1.02, chloroform).

来源