Water → 3alpha-Acetoxy-5alpha-pregnane-11,20-dione

HRID 1973740Notes

Reaction equation

HRID 1973740 reaction equation
[OH:1][C@@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[C:17](=[O:23])[CH2:16][C@@:15]2([CH3:24])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.[C:25](OC(=O)C)(=[O:27])[CH3:26].O>N1C=CC=CC=1>[C:25]([O:1][C@@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[C:17](=[O:23])[CH2:16][C@@:15]2([CH3:24])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1)(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 104845Alphaxalone

Product 1

HCID 118727973alpha-Acetoxy-5alpha-pregnane-11,20-dione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3α-hydroxy-5α-pregnane-11,20-dione (1 g) in pyridine (ca 5 ml) was treated with acetic anhydride (2.5 ml) and allowed to stand overnight. The reaction mixture was poured into water and the solid collected by filtration and dried to give the title compound m.p. 150°-151°.

Workup

  1. filtrationthe solid collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-25e966eb05ea4922a5fa0331b4c1c324
Source dataset
uspto-grants-1976_12
Patent number
US03998829

Reaction notes

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