Reacción #448844

Ecuación de reacción

triphenylphosphine

carbon tetrachloride

7α-(5-hydroxypentyl)-estr-4-ene-3,17-dione

bicarbonate

→

7α-(5-chloropentyl)-estr-4-ene-3,17-dione

Disolventes

acetonitrile

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Secadodried with sodium sulfate
2. 2
   Concentraciónconcentrated by evaporation in a vacuum
3. 3
   OtroThe residue is chromatographed on silica gel with dichloromethane and ethyl acetate

Procedimiento

The same product is obtained from 8.05 g of 7α-(5-hydroxypentyl)-estr-4-ene-3,17-dione (Example 1b) by a 3.5-hour reaction with 8.66 g of triphenylphosphine in 85 ml of carbon tetrachloride and 30 ml of acetonitrile at room temperature. The reaction mixture is diluted with dichloromethane, shaken out with saturated bicarbonate solution and with saturated common salt solution, dried with sodium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel with dichloromethane and ethyl acetate, whereby 4.08 g of 7α-(5-chloropentyl)-estr-4-ene-3,17-dione is obtained, [α]D22 =+68°(c=0.5% in chloroform)

Fuente