反应 #2652

反应方程式

lithium hydroxide monohydrate

chloroform

(-)-acetic acid cis-4-benzyloxy-cyclopent-2-enyl ester

water

→

title compound

收率 92.8%

(+)-cis-4-benzyloxy-cyclopent-2-enol

收率 92.8%

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, 2 g, 20% ethyl acetate/hexane, 1.5×2.5 cm column)

实验过程

Dissolve (-)-acetic acid cis-4-benzyloxy-cyclopent-2-enyl ester (158 mg, 0.68 mmol, prepared in example 17) in THF/methanol/water (1.5/0.5/0.5 mL). Add lithium hydroxide monohydrate (0.75 mmol) with stirring. After stirring for about 2 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, 2 g, 20% ethyl acetate/hexane, 1.5×2.5 cm column) to provide the title compound (120 mg, 92% yield), [α]20D =+5.0°, (C=0.93, chloroform).

来源