Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 11beta-Fluoro-3-methoxy-7alpha-methylestra-3,5-dien-17-one

HRID 855482Notes

Reaction equation

HRID 855482 reaction equation
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C@@H:4]1[C:9]([CH2:10][C@H:11]2[CH3:21])=[CH:8][C:7](=[O:22])[CH2:6][CH2:5]1.S([C:27]1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1>COC(OC)(C)C.C(OCC)(=O)C>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C@@H:4]1[C:9](=[CH:10][C@H:11]2[CH3:21])[CH:8]=[C:7]([O:22][CH3:27])[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10193144HCID 10193144, compound

Product 1

HCID 6933295211beta-Fluoro-3-methoxy-7alpha-methylestra-3,5-dien-17-oneYield 789.2%

Reagents, catalysts & solvents 2

HCID 64952,2-DimethoxypropaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2 g of 11β-fluoro-7α-methylestr-4-ene-3,17-dione in 20 ml 2,2-di-methoxypropane was stirred with 200 mg of pyridinium tosylate for 6.5 hours at 80° C. Then, it was diluted with ethyl acetate, washed with sodium bicarbonate solution and sodium chloride solution, dried on sodium sulfate and concentrated by evaporation in a vacuum. 2 g of crude 11β-fluoro-3-methoxy-7α-methylestra-3,5-dien-17-one was obtained.

Workup

  1. washwashed with sodium bicarbonate solution and sodium chloride solution
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-7f25abc367b147e4b979bfc1d1e0252f
Source dataset
uspto-grants-2007_08
Patent number
US07262023B2

Reaction notes

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