Acetic Anhydride → 19-Hydroxy-4-methyl-4-androstene3,17-dione acetate

HRID 2398004Notes

Reaction equation

HRID 2398004 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=[C:7]([CH3:22])[C:6](=[O:23])[CH2:5][CH2:4]2.[C:24]([O:27]C(=O)C)(=[O:26])[CH3:25]>N1C=CC=CC=1>[C:24]([OH:27])(=[O:26])[CH3:25].[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=[C:7]([CH3:22])[C:6](=[O:23])[CH2:5][CH2:4]2

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 5379505019-Hydroxy-4-methyl-4-androstene-3,17-dione

Product 1

HCID 8673474619-Hydroxy-4-methyl-4-androstene3,17-dione acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

19-Hydroxy-4-methyl-4-androstene-3,17-dione is stirred under nitrogen with acetic anhydride and pyridine for about 16 hours. The yellow solution is poured onto water and the precipitate collected by suction filtration and washed well with water. Crystallization from acetone-hexane yields the desired 19-hydroxy-4-methyl-4-androstene-3,17-dione acetate.

Workup

  1. additionThe yellow solution is poured onto water
  2. filtrationthe precipitate collected by suction filtration
  3. washwashed well with water
  4. customCrystallization from acetone-hexane

Sources & evidence

ORD record
ord-39c5f48a2703496d8aaea8af3010e5a5
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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