Reacción #346406

Ecuación de reacción

chloroform

sodium trifluoroacetate

sodium fluoride

sodium trifluoroacetate

fluorine

fluorine

3β-Acetoxy-5α,6β-dichloropregnan-20-one

→

3β-acetoxy-5α,6β-dichloro-14α-fluoropregnan-20-one

Disolventes

fluorotrichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe resulting solution was cooled to -78°
2. 2
   Otrowas bubbled through the solution over a period of 8 hours
3. 3
   workup.ADDITIONThe reaction solution was then poured into aqueous sodium thiosulphate
4. 4
   Otrothe organic layer was separated
5. 5
   Lavadowashed with water
6. 6
   Secadodried over potassium carbonate
7. 7
   Otroevaporated to dryness

Procedimiento

3β-Acetoxy-5α,6β-dichloropregnan-20-one (1.4g) was dissolved in fluorotrichloromethane (250 ml) and chloroform (200 ml) containing sodium trifluoroacetate (ca. 2g) and sodium fluoride (ca. 2g). The resulting solution was cooled to -78° and vigourously stirred, whereupon fluorine from four 750 cc bottles (10% v/v fluorine in nitrogen) was bubbled through the solution over a period of 8 hours. The reaction solution was then poured into aqueous sodium thiosulphate and the organic layer was separated, washed with water, dried over potassium carbonate and evaporated to dryness to yield crude 3β-acetoxy-5α,6β-dichloro-14α-fluoropregnan-20-one.

Fuente