Reacción #362816

Ecuación de reacción

8

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

sodium borohydride

HCl

→

9

Rendimiento 99.1%

2-Methyl-6-tert-butylindene

Rendimiento 99.1%

Disolventes

tetrahydrofuran methanol

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente