反応 #1353

反応方程式

acetone

sodium borohydride

2-ethyl-4-phenyl-1-indanone

sodium borohydride

→

desired product

収率 100.1%

2-ethyl-1-hydroxy-4-phenylindene

収率 100.1%

溶媒

ethanol

ethanol

反応条件

後処理

1. 1
   その他A 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
   その他of was elevated to 50° C.
5. 5
   濃縮Then, the reaction mixture was concentrated under reduced pressure
6. 6
   workup.DISSOLUTIONdissolved in 50 ml of water
7. 7
   抽出extracted with 50 ml of ether
8. 8
   その他After the organic phase was separated
9. 9
   抽出the aqueous phase was extracted with 50 ml of ether two times
10. 10
    洗浄The combined organic phase was washed with 100 ml of a saturated aqueous solution of sodium chloride
11. 11
    乾燥by drying over anhydrous Na2SO4
12. 12
    その他The solvent was evaporated under reduced pressure

実験手順

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%).

出典