Tetrahydrofuran → HCID 86760341, compound
Reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:27])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=CC=1.[CH3:28][O:29][C:30](=O)[O:31]C.[H-].[K+].C1C[O:39]CC1>>[O:39]1[CH2:5][CH2:6][CH2:7][CH2:2][CH:1]1[O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:27])[C@H:17]([C:30]([O:29][CH3:28])=[O:31])[CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1Participants
5
Procedure
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.
Workup
- temperatureThen, the mixture was heated
- temperatureto reflux for a period of 3 h
- customMost of the solvent was then evaporated
- additionthe residue was diluted with ethyl acetate (100 mL)
- additiontreated with a saturated ammonium chloride solution (50 mL)
- washThe organic phase was washed with water (6×40 mL)
- customdried
- customevaporated
- customto give a yellowish solid
Sources & evidence
- ORD record
- ord-f34e058ff49b4be193850192d54bb9bd
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07153844B2
Reaction notes
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