Acetic Acid → 11beta-Fluoro-7alpha-(5-hydroxypentyl)-estr4-ene-3,17-dione

HRID 650346Notes

Reaction equation

HRID 650346 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[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][Si](C(C)(C)C)(C)C)=[CH:8][C:7](=[O:34])[CH2:6][CH2:5]1.C(O)(=O)C>C1COCC1.O>[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[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])=[CH:8][C:7](=[O:34])[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 1587066011beta-Fluoro-7alpha-(5-tert-butyl-dimethylsilyloxypentyl)oestr-4-ene-3,17-dione

Product 1

HCID 1587066111beta-Fluoro-7alpha-(5-hydroxypentyl)-estr4-ene-3,17-dioneYield 115.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 23.1 g of 11β-fluoro-7α-(5-tert-butyl-dimethylsilyloxypentyl)-estr-4-ene-3,17-dione in 115 ml of THF and 64 ml of water are stirred with 128 ml of glacial acetic acid for 2.5 hours at 50° C. The reaction mixture is concentrated by evaporation in a vacuum, taken up in ethyl acetate, washed with water and dried. 20.4 g of 11β-fluoro-7α-(5-hydroxypentyl)-estr-4-ene-3,17-dione is obtained as foam.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation in a vacuum
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-7d64993dad5c42739faf722ed14cdf7a
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

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