Water → 7alpha-(5-Acetoxypentyl)-11beta-fluorooestr-4-ene-3,17-dione

HRID 650347Notes

Reaction equation

HRID 650347 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][OH:26])=[CH:8][C:7](=[O:27])[CH2:6][CH2:5]1.[C:28](OC(=O)C)(=[O:30])[CH3:29].O>N1C=CC=CC=1>[C:28]([O:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C@@H:11]1[CH2:10][C:9]2[C@H:4]([CH2:5][CH2:6][C:7](=[O:27])[CH:8]=2)[C@@H:3]2[C@@H:12]1[C@H:13]1[C@@:17]([CH2:19][C@@H:2]2[F:1])([CH3:18])[C:16](=[O:20])[CH2:15][CH2:14]1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 1587066111beta-Fluoro-7alpha-(5-hydroxypentyl)-estr4-ene-3,17-dione

Product 1

HCID 699353277alpha-(5-Acetoxypentyl)-11beta-fluorooestr-4-ene-3,17-dione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

20 g of 11β-fluoro-7α-(5-hydroxypentyl)-estr-4-ene-3,17-dione in 100 ml of pyridine can be reacted over a period of 2 hours with 50 ml of acetic anhydride at 25° C. Then, 5 ml of water is added at 0° C., and it is stirred for 45 minutes. It is extracted with diethyl ether, washed with 2N sulfuric acid, pyridine-free, and the solution is neutralized in succession with saturated sodium bicarbonate solution and water. After drying and concentration by evaporation in a vacuum, the crude product is chromatographed on silica gel with a hexane-ethyl acetate-gradient. 17 g of 7α-(5-acetoxypentyl)-11β-fluoro-estr-4-ene-3,17-dione with a melting point of 78.4° C. is obtained.

Workup

  1. extractionIt is extracted with diethyl ether
  2. washwashed with 2N sulfuric acid, pyridine-free
  3. customAfter drying
  4. concentrationconcentration
  5. customby evaporation in a vacuum
  6. customthe crude product is chromatographed on silica gel with a hexane-ethyl acetate-gradient

Sources & evidence

ORD record
ord-891df873486541fc9234eea26a3eee99
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

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