Reacción #55918

Ecuación de reacción

water

sodium hydride

2,3-dihydro-5-methoxy-3,3-dimethylbenzofuran

ethanethiol

→

2,3-dihydro-3,3-dimethyl-benzofuran-5-ol

Disolventes

dimethyl formamide

dimethyl formamide

dimethyl formamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaunder reflux in a nitrogen atmosphere for 3 hours
2. 2
   Lavadothe aqueous phase washed with chloroform
3. 3
   Extracciónextracted into ether
4. 4
   OtroThe ether was evaporated off

Procedimiento

A solution of ethanethiol (12.6 parts) in dimethyl formamide (60 parts) was added with stirring under nitrogen over a period of 20 minutes to a mixture of sodium hydride (6.6 parts of 80% dispersion in oil) and dry dimethyl formamide (60 parts) cooled to 0° C. After 10 minutes, a solution of 2,3-dihydro-5-methoxy-3,3-dimethylbenzofuran (18 parts) in dimethyl formamide (40 parts) was added and the mixture boiled under reflux in a nitrogen atmosphere for 3 hours. The mixture was then added to water and the aqueous phase washed with chloroform, acidified with hydrochloric acid and extracted into ether. The ether was evaporated off to yield 2,3-dihydro-3,3-dimethyl-benzofuran-5-ol (5.4 parts) as a brown oil.

Fuente