Réaction #947056

Équation de réaction

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

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

dimethylcarbonate

potassium hydride

THF

THF

→

title compound

Rendement 90.0%

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

Rendement 90.0%

Conditions de réaction

Traitement

1. 1
   TempératureThen, the mixture was heated
2. 2
   Températureto reflux for a period of 3 h
3. 3
   AutreMost 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
   LavageThe organic phase was washed with water (6×40 mL)
7. 7
   Autredried
8. 8
   Autreevaporated
9. 9
   Autreto give a yellowish solid

Mode opératoire

A solution of 3-tetrahydropyranyloxy-1,3,5(10)-estratrien-17-one (2, R=THP) (6.58 g, 18.2 mmol) in dry THF (50 mL) was added over a period of 20 min to a solution of dimethylcarbonate (3.98 mL, 47.23 mmol) and potassium hydride (2.27 g (3.6 g, 70% in oil), 56.68 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.

Source