Dimethyl Carbonate → HCID 86760340, compound

HRID 859871Notes

Reaction equation

HRID 859871 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]=[CH:4][CH:3]=1.[CH3:28][O:29][C:30](=O)[O:31]C.[H-].[K+]>C1COCC1>[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])[C@H:17]([C:30]([O:29][CH3:28])=[O:31])[CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 12021Dimethyl CarbonateHCID 82127Potassium hydrideHCID 11132151(8R,9S,13S,14S)-13-methyl-3-phenylmethoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one

Product 1

HCID 86760340HCID 86760340, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  1. temperatureThen, the mixture was heated
  2. temperatureto reflux for a period of 3 h
  3. customMost of the solvent was then evaporated
  4. additionthe residue was diluted with ethyl acetate (100 mL)
  5. additiontreated with a saturated ammonium chloride solution (50 mL)
  6. washThe organic phase was washed with water (6×40 mL)
  7. customdried
  8. customevaporated
  9. customto give a yellowish solid

Sources & evidence

ORD record
ord-f01b2e81059140ec8bf550e76f31cc46
Source dataset
uspto-grants-2006_12
Patent number
US07153844B2

Reaction notes

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