17beta-(Hydroxymethyl)androst-4-ene-3-ol → HCID 14377617, compound

HRID 1708897

Reaction equation

HRID 1708897 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:19]([CH2:20][CH2:21][C@:4]12[CH3:5])[C@:17]1([CH3:18])[C:12](=[CH:13][CH:14]([OH:22])[CH2:15][CH2:16]1)[CH2:11][CH2:10]3>ClC(Cl)Cl.[O-2].[O-2].[Mn+4]>[O:22]=[C:14]1[CH2:15][CH2:16][C@@:17]2([CH3:18])[C:12]([CH2:11][CH2:10][C@@H:9]3[C@@H:19]2[CH2:20][CH2:21][C@@:4]2([CH3:5])[C@H:6]3[CH2:7][CH2:8][C@@H:3]2[CH2:2][OH:1])=[CH:13]1

Participants

4

Reactant 1

HCID 1480133417beta-(Hydroxymethyl)androst-4-ene-3-ol

Product 1

HCID 14377617HCID 14377617, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 17β-(hydroxymethyl)-androst-4-ene-3-ol (27 g, 0.089 mol) in 1200 ml trichloromethane was treated with activated manganese dioxide (66 g). After 3 hours the mixture was filtered. Concentration afforded 26 g (96%) of 3-oxo-17β-(hydroxymethyl)-4androstene (m.p. 151° C.).

Workup

  1. filtrationAfter 3 hours the mixture was filtered
  2. concentrationConcentration

Sources & evidence

ORD record
ord-8ee8a3c67fd340aa93ac5c712520c99e
Source dataset
uspto-grants-1990_08
Patent number
US04946834

Linked notes

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