反应 #362815

反应方程式

sodium borohydride

1

(±)-2-Methyl-5-isobutyl-1-indanone

HCl

→

2

收率 95.0%

2-Methyl-6-isobutylindene

收率 95.0%

溶剂

tetrahydrofuran methanol

反应条件

后处理

1. 1
   萃取the mixture was extracted 3 times with 50 ml of diethyl ether in each case
2. 2
   干燥The combined organic phases were dried (MgSO4)
3. 3
   其他freed from solvent on a rotary evaporator
4. 4
   workup.ADDITION0.4 g of p-toluenesulfonic acid was added
5. 5
   温度the mixture was refluxed for 2 hours
6. 6
   洗涤The reaction mixture was washed twice with 50 ml of saturated aqueous NaHCO3 solution in each case
7. 7
   其他freed from solvent on a rotary evaporator
8. 8
   其他The residue was purified by chromatography on 400 g of silica gel (hexane)

实验过程

2.4 g (62 mmol) of sodium borohydride were added to a solution of 8.3 g (41 mmol) of 1 in 50 ml of tetrahydrofuran/methanol (2:1), and the mixture was stirred at room temperature for 16 hours. 50 ml of conc. aqueous HCl were subsequently added, and the mixture was extracted 3 times with 50 ml of diethyl ether in each case. The combined organic phases were dried (MgSO4) and freed from solvent on a rotary evaporator. The residue was taken up in 100 ml of toluene, 0.4 g of p-toluenesulfonic acid was added, and the mixture was refluxed for 2 hours. The reaction mixture was washed twice with 50 ml of saturated aqueous NaHCO3 solution in each case and freed from solvent on a rotary evaporator. The residue was purified by chromatography on 400 g of silica gel (hexane), giving 7.17 g (95%) of 2 as a colorless oil.

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