反応 #1359

反応方程式

sodium boron hydride

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

→

desired product

収率 96.4%

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

収率 96.4%

溶媒

ethanol

ethanol

反応条件

後処理

1. 1
   その他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
   濃縮Then, the reaction mixture was concentrated under reduced pressure, which
5. 5
   抽出was then extracted with 150 ml of water and 150 ml of ether
6. 6
   その他The organic phase was separated
7. 7
   抽出the aqueous phase was further extracted with 100 ml of ether
8. 8
   洗浄The combined organic phase was washed with 100 ml of a saturated NaCl aq. two times
9. 9
   乾燥by dried over anhydrous Na2SO4
10. 10
    その他The solvent was evaporated under reduced pressure

実験手順

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.

出典