反应 #1359

反应方程式

sodium boron hydride

4-bromo-2-i-butyl-1-indanone

→

desired product

收率 96.4%

4-bromo-2-i-butyl-1-hydroxyindane

收率 96.4%

溶剂

ethanol

ethanol

反应条件

后处理

1. 1
   其他A 300-ml three-necked round flask equipped with a stirring bar
2. 2
   workup.ADDITIONTo the mixture was added dropwise a solution
3. 3
   workup.ADDITIONAfter the addition
4. 4
   浓缩Then, the reaction mixture was concentrated under reduced pressure, which
5. 5
   萃取was then extracted with 150 ml of water and 150 ml of ether
6. 6
   其他The organic phase was separated
7. 7
   萃取the aqueous phase was further extracted with 100 ml of ether
8. 8
   洗涤The combined organic phase was washed with 100 ml of a saturated NaCl aq. two times
9. 9
   干燥by dried over anhydrous Na2SO4
10. 10
    其他The solvent was evaporated under reduced pressure

实验过程

A 300-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a dropping funnel and a thermometer was charged with 2.51 g (66.3 mmol) of sodium boron hydride and 85 ml of ethanol. To the mixture was added dropwise a solution containing 37.0 g (132.6 mmol) of the above-obtained 4-bromo-2-i-butyl-1-indanone dissolved in 55 ml of ethanol at room temperature under a nitrogen atmosphere. After the addition was completed, the mixture was further stirred for 16 hours. Then, the reaction mixture was concentrated under reduced pressure, which was then extracted with 150 ml of water and 150 ml of ether. The organic phase was separated, and the aqueous phase was further extracted with 100 ml of ether. The combined organic phase was washed with 100 ml of a saturated NaCl aq. two times, followed by dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to obtain 34.4 g of the desired product (mixture of two isomers) as a pale yellow solid (yield: 96%). This alcohol was used in the next reaction without further purification.

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