Reacción #362815

Ecuación de reacción

sodium borohydride

1

(±)-2-Methyl-5-isobutyl-1-indanone

HCl

→

2

Rendimiento 95.0%

2-Methyl-6-isobutylindene

Rendimiento 95.0%

Disolventes

tetrahydrofuran methanol

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente