Water → 3-Acetoxy-5-androstene-17-one

HRID 362767Notes

Reaction equation

HRID 362767 reaction equation
[CH3:1][C@@:2]12[C:10](=[O:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH:13]=[C:14]3[CH2:19][C@@H:18]([OH:20])[CH2:17][CH2:16][C@:15]3([CH3:21])[C@H:5]1[CH2:4][CH2:3]2.[OH2:22].N1[CH:28]=[CH:27]C=CC=1>>[C:27]([O:20][CH:18]1[CH2:17][CH2:16][C@@:15]2([CH3:21])[C:14](=[CH:13][CH2:12][C@@H:6]3[C@@H:5]2[CH2:4][CH2:3][C@@:2]2([CH3:1])[C@H:7]3[CH2:8][CH2:9][C:10]2=[O:11])[CH2:19]1)(=[O:22])[CH3:28]

Participants

4

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 5881Dehydroepiandrosterone

Product 1

HCID 117593183-Acetoxy-5-androstene-17-one

Procedure

Dehydroepiandrosterone (2.88 g, 10 mmol) is dissolved in a mixture (100 ml) of anhydride acetic and pyridine (1:1 v/v) and left at room temperature for 16 h. The mixture is then poured carefully into iced water and after 16 h, crystals are filtered and dried in vacuo.

Workup

  1. filtrationcrystals are filtered
  2. customdried in vacuo

Sources & evidence

ORD record
ord-3994d56ec26e4fdfaf58623d80a5a6d2
Source dataset
uspto-grants-1999_02
Patent number
US05872114

Reaction notes

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