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

HRID 973090Notes

Reaction equation

HRID 973090 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-e3303b52044f40428299bae3071deff0
Source dataset
uspto-grants-1977_10
Patent number
US04054651

Reaction notes

Loading…