Reacción #95556

Ecuación de reacción

HCl

Sodium borohydride

cis 2-(1-hydroxy-2,2,2-trichloroethyl)-3,3-dimethylcyclopropane carboxylic acid

sodium borohydride

→

desired product

Rendimiento 25.0%

4-dichloromethyl-6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one

Rendimiento 25.0%

Disolventes

dimethylformamide

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was heated for a further 15 minutes at 80° C
2. 2
   Extracciónextracted with deuterochloroform, CDCl3
3. 3
   LavadoThe extract was washed with water and analysed by NMR, which

Procedimiento

Sodium borohydride (0.12 mmol) was added to a solution of cis 2-(1-hydroxy-2,2,2-trichloroethyl)-3,3-dimethylcyclopropane carboxylic acid (0.12 mol) in dry dimethylformamide (0.4 ml), and the mixture was heated for 30 minutes at 80° C. An additional amount of 0.12 mmol sodium borohydride was then added and the mixture was heated for a further 15 minutes at 80° C. It was then diluted with water, acidified with concentrated HCl and extracted with deuterochloroform, CDCl3. The extract was washed with water and analysed by NMR, which showed a yield of 25% of the desired product, with 30% of unconverted starting material.

Fuente