Water → Androstenediol 3,17-diacetate

HRID 1808753

Reaction equation

HRID 1808753 reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH:9]=[C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C@H:12]([OH:20])[CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[OH:21].[C:22](OC(=O)C)(=[O:24])[CH3:23].N1[CH:34]=[CH:33]C=CC=1.[OH2:35]>>[C:22]([O:20][C@H:12]1[CH2:13][CH2:14][C@@:15]2([CH3:16])[C:10](=[CH:9][CH2:8][C@@H:7]3[C@@H:17]2[CH2:18][CH2:19][C@@:2]2([CH3:1])[C@H:6]3[CH2:5][CH2:4][C@@H:3]2[O:21][C:33](=[O:35])[CH3:34])[CH2:11]1)(=[O:24])[CH3:23]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 10634Androstenediol

Product 1

HCID 102205Androstenediol 3,17-diacetateYield 81.3%

Procedure

A mixture of 5-androstene-3β,17β-diol (1 g, 3.44 mmol), acetic anhydride (2 Ml) and dry pyridine (4 Ml) was heated in a steam bath for 2 h, and poured into iced water. The precipitate was filtered, washed with water, dried and crystallized in methanol to afford the product 5-androstene-3β,17β-diol diacetate (1 g, 81.3%), mp 163-165° C. [Singh H., et al Indian J. Chem. 1969, 7, 1084-1087].

Workup

  1. temperaturewas heated in a steam bath for 2 h
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried
  5. customcrystallized in methanol

Sources & evidence

ORD record
ord-3d77544b8abb416d87bb9e36526edc2c
Source dataset
uspto-grants-2013_01
Patent number
US08361996B2

Linked notes

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