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

HRID 839590Notes

Reaction equation

HRID 839590 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

A solution of 19-hydroxyandrost-4-ene-3,17-dione in acetic anhydride and pyridine is allowed to stand overnight after which the reaction mixture is poured into ice water. The resulting solid is collected, dried and recrystallized from hexane to give 19-acetoxyandrost-4-ene-3,17-dione.

Workup

  1. customThe resulting solid is collected
  2. customdried
  3. customrecrystallized from hexane

Sources & evidence

ORD record
ord-acede2d498dc4811b126f80b833c4225
Source dataset
uspto-grants-1978_06
Patent number
US04096254

Reaction notes

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