Water → 19-Acetoxyandrost-4-en-3,17-dione

HRID 2412833Notes

Reaction equation

HRID 2412833 reaction equation
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:22])[CH2:5][CH2:4]2.[C:23](OC(=O)C)(=[O:25])[CH3:24].O>N1C=CC=CC=1>[C:23]([O:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:22])[CH2:5][CH2:4]2)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 25237919-Hydroxyandrostenedione

Product 1

HCID 1294241219-Acetoxyandrost-4-en-3,17-dione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

19-Hydroxyandrost-4-ene-3,17-dione (50 g) dissolved in 100 ml of pyridine and 250 ml of acetic anhydride was swirled while being warmed on a steam bath. When solution was complete, the reaction was allowed to stand at room temperature. After two hours ice and water were added and the resultant oil was extracted into ethyl acetate. The organic phase was washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo to give 58 g of the title compound as an amorphous solid. The product, homogeneous by thin-layer chromatography using 1:1 ethyl acetate/Skellysolve B on silica gel, was employed for subsequent reactions without further purification.

Workup

  1. temperaturewhile being warmed on a steam bath
  2. customto stand at room temperature
  3. extractionthe resultant oil was extracted into ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-63c03300bd7f4eab829fc7a9b2d8002d
Source dataset
uspto-grants-1985_01
Patent number
US04495102

Reaction notes

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