Reaktion #362816

Reaktionsgleichung

8

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

sodium borohydride

HCl

→

9

Ausbeute 99.1%

2-Methyl-6-tert-butylindene

Ausbeute 99.1%

Lösungsmittel

tetrahydrofuran methanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle