Acetic Anhydride → 19-Acetoxyandrost-4-en-3,17-dione

HRID 326984

Reaction equation

HRID 326984 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]>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

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 25237919-Hydroxyandrostenedione

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Androst-4-en-19-ol-3,17-dione (11) is treated with acetic anhydride (Ac2O, b) in pyridine. Aqueous work-up is followed by extraction and purification to yield the acetate (14).

Workup

  1. extractionAqueous work-up is followed by extraction and purification

Sources & evidence

ORD record
ord-7fda3844403d4eed8d5f46d4eaae5408
Source dataset
uspto-grants-1993_12
Patent number
US05272134

Linked notes

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