반응 #947053

반응 방정식

3-benzyloxy-1,3,5(10)-estratrien-17-one

dimethylcarbonate

potassium hydride

→

title compound

수율 90.0%

3-benzyloxy-16α,β-(methoxycarbonyl)-1,3,5(10)-estratrien-17-one

수율 90.0%

용매

THF

THF

반응 조건

후처리

1. 1
   온도Then, the mixture was heated
2. 2
   온도to reflux for a period of 3 h
3. 3
   기타Most of the solvent was then evaporated
4. 4
   workup.ADDITIONthe residue was diluted with ethyl acetate (100 mL)
5. 5
   workup.ADDITIONtreated with a saturated ammonium chloride solution (50 mL)
6. 6
   세척The organic phase was washed with water (6×40 mL)
7. 7
   기타dried
8. 8
   기타evaporated
9. 9
   기타to give a yellowish solid

실험 절차

A solution of 3-benzyloxy-1,3,5(10)-estratrien-17-one (2) (4.00 g, 11.1 mmol) in dry THF (5 mL) was added over a period of 30 min to a solution of dimethylcarbonate (2.34 mL, 27.8 mmol) and potassium hydride (1.42 g, 34.7 mmol) in dry THF (40 mL). Then, the mixture was heated to reflux for a period of 3 h. Most of the solvent was then evaporated and the residue was diluted with ethyl acetate (100 mL) and treated with a saturated ammonium chloride solution (50 mL). The organic phase was washed with water (6×40 mL), dried and evaporated to give a yellowish solid. Trituration of the residue with a mixture of acetone:hexanes (1:1) yielded the title compound in 90% yield as a white solid.

출처