Reacción #93007

Ecuación de reacción

cyclohexanecarboxylic acid

NaOH

16β-ethyl-17β-bromoacetoxy-4-estren-3-one

DMF

→

above-identified compound

Rendimiento 88.2%

16β-Ethyl-17β-cyclohexanecarbonyloxyacetoxy-4-estren-3-one

Rendimiento 88.2%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture is refluxed for 5 hours
2. 2
   workup.ADDITIONtreated in the same manner as Example 26
3. 3
   OtroThe reaction mixture is then chromatographed on a silica gel column
4. 4
   Lavadopassage of 200 ml of n-hexane-diisopropyl ether (6:4), elution
5. 5
   workup.ADDITIONis carried out with 600 ml of a 1:1 mixture of the same solvents
6. 6
   OtroThe eluate is evaporated under reduced pressure
7. 7
   Otroto remove the solvent

Procedimiento

In 20 ml of acetone is dissolved 0.64 g of cyclohexanecarboxylic acid, and 2.5 ml of 2N-NaOH and then 1.0 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 20 ml of DMF are serially added to the above solution. The mixture is refluxed for 5 hours, and thereafter treated in the same manner as Example 26. The reaction mixture is then chromatographed on a silica gel column. Following passage of 200 ml of n-hexane-diisopropyl ether (6:4), elution is carried out with 600 ml of a 1:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 0.98 g of the above-identified compound as a light-yellow viscous oil.

Fuente