反応 #362816

反応方程式

8

(+)-2-Methyl-6-tert-butylindan-1-one

sodium borohydride

HCl

→

9

収率 99.1%

2-Methyl-6-tert-butylindene

収率 99.1%

溶媒

tetrahydrofuran methanol

反応条件

後処理

1. 1
   workup.ADDITIONwas added to pH 1
2. 2
   抽出the mixture was extracted a number of times with diethyl ether
3. 3
   洗浄The combined organic phases were washed with saturated aqueous NaHCO3 solution and NaCl solution
4. 4
   乾燥dried (MgSO4)
5. 5
   その他The solvent was removed in vacuo
6. 6
   その他the crude product, without further purification
7. 7
   workup.ADDITION0.1 g of p-TsOH was added
8. 8
   温度the mixture was refluxed for 1 hour
9. 9
   洗浄The reaction mixture was washed with 100 ml of saturated aqueous NaHCO3 solution
10. 10
    その他the solvent was removed in vacuo
11. 11
    ろ過The crude product was purified by filtration through 200 g of silica gel (hexane)

実験手順

5.3 g (26 mmol) of 8 were dissolved in 50 ml of tetrahydrofuran/methanol (2:1), 1.5 g of sodium borohydride were added at 0° C. with magnetic stirring, and the mixture was stirred at room temperature for 18 hours. The reaction mixture was poured onto ice, conc. HCl was added to pH 1, and the mixture was extracted a number of times with diethyl ether. The combined organic phases were washed with saturated aqueous NaHCO3 solution and NaCl solution and dried (MgSO4). The solvent was removed in vacuo, and the crude product, without further purification, was taken up in 300 ml of toluene, 0.1 g of p-TsOH was added, and the mixture was refluxed for 1 hour. The reaction mixture was washed with 100 ml of saturated aqueous NaHCO3 solution, and the solvent was removed in vacuo. The crude product was purified by filtration through 200 g of silica gel (hexane), giving 4.8 g (99%) of 9 as a colorless oil.

出典