반응 #1359

반응 방정식

sodium boron hydride

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

→

desired product

수율 96.4%

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

수율 96.4%

용매

ethanol

ethanol

반응 조건

후처리

1. 1
   기타A 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
   농축Then, the reaction mixture was concentrated under reduced pressure, which
5. 5
   추출was then extracted with 150 ml of water and 150 ml of ether
6. 6
   기타The organic phase was separated
7. 7
   추출the aqueous phase was further extracted with 100 ml of ether
8. 8
   세척The combined organic phase was washed with 100 ml of a saturated NaCl aq. two times
9. 9
   건조by dried over anhydrous Na2SO4
10. 10
    기타The solvent was evaporated under reduced pressure

실험 절차

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.

출처