HCID 69104771, compound → HCID 68657772, compound

HRID 2224049Notes

Reaction equation

HRID 2224049 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@:8]([CH:22]=[CH2:23])([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C@@H:12]([OH:21])[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@:8]([CH:22]=[CH2:23])([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C:12](=[O:21])[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 69104771HCID 69104771, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 68657772HCID 68657772, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 700 mg of 3-methoxy-8β-vinyl-estra-1,3,5(10)-trien-17β-ol in 30 ml of dichloromethane was mixed with 740 mg of pyridinium chlorochromate and stirred for 3 hours at room temperature. By filtration of the reaction mixture on silica gel (solvent mixture: cyclohexane/ethyl acetate=7/3) and subsequent concentration by evaporation of the filtrate in a rotary evaporator, 680 mg (98%) of 3-methoxy-8β-vinyl-estra-1,3,5(10)-trien-17-one was obtained as almost colorless foam, which was used in the next stage without further purification.

Workup

  1. filtrationBy filtration of the reaction mixture
  2. concentrationon silica gel (solvent mixture: cyclohexane/ethyl acetate=7/3) and subsequent concentration
  3. customby evaporation of the filtrate
  4. customin a rotary evaporator

Sources & evidence

ORD record
ord-1d1fbf05deb046d481d73d10d63f8210
Source dataset
uspto-grants-2008_05
Patent number
US07378404B2

Reaction notes

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