반응 #362816

반응 방정식

8

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

sodium borohydride

HCl

→

9

수율 99.1%

2-Methyl-6-tert-butylindene

수율 99.1%

용매

tetrahydrofuran methanol

반응 조건

후처리

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

실험 절차

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.

출처