반응 #1353

반응 방정식

acetone

sodium borohydride

2-ethyl-4-phenyl-1-indanone

sodium borohydride

→

desired product

수율 100.1%

2-ethyl-1-hydroxy-4-phenylindene

수율 100.1%

용매

ethanol

ethanol

반응 조건

후처리

1. 1
   기타A 200-ml three-necked round flask equipped with a stirring bar
2. 2
   workup.ADDITIONTo the mixture was dropwise added a solution
3. 3
   workup.ADDITIONAfter the addition
4. 4
   기타of was elevated to 50° C.
5. 5
   농축Then, the reaction mixture was concentrated under reduced pressure
6. 6
   workup.DISSOLUTIONdissolved in 50 ml of water
7. 7
   추출extracted with 50 ml of ether
8. 8
   기타After the organic phase was separated
9. 9
   추출the aqueous phase was extracted with 50 ml of ether two times
10. 10
    세척The combined organic phase was washed with 100 ml of a saturated aqueous solution of sodium chloride
11. 11
    건조by drying over anhydrous Na2SO4
12. 12
    기타The solvent was evaporated under reduced pressure

실험 절차

A 200-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a dropping funnel and a thermometer was charged with 0.85 g (22.6 mmol) of sodium borohydride and 28 ml of ethanol. To the mixture was dropwise added a solution containing 10.6 g (45.1 mmol) of the above-obtained 2-ethyl-4-phenyl-1-indanone dissolved in 20 ml of ethanol at room temperature under a nitrogen atmosphere. After the addition was completed, the temperature of was elevated to 50° C., and the reaction mixture was stirred for 3.5 hours. After the reaction was completed, the unreacted sodium borohydride was decomposed by acetone. Then, the reaction mixture was concentrated under reduced pressure, and then dissolved in 50 ml of water and extracted with 50 ml of ether. After the organic phase was separated, the aqueous phase was extracted with 50 ml of ether two times. The combined organic phase was washed with 100 ml of a saturated aqueous solution of sodium chloride, followed by drying over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to obtain 10.67 g of the desired product as a pasty pale yellow liquid (mixture of two kinds of isomers) (yield; 99%).

출처