Methyl iodide → 3Oxo-17beta-(hydroxymethyl)-4-methyl-4-androstene

HRID 1708905Notes

Reaction equation

HRID 1708905 reaction equation
[CH3:1]C(C)([O-])C.[K+].[O:7]=[C:8]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@H:14]3[CH2:15][CH2:16][C@@H:17]2[CH2:27][OH:28])=[CH:9]1.CI>C(O)(C)(C)C>[O:7]=[C:8]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@H:14]3[CH2:15][CH2:16][C@@H:17]2[CH2:27][OH:28])=[C:9]1[CH3:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 1437761717beta-Hydroxymethyl-4-androsten-3-onHCID 23665647Potassium tert-butoxide

Product 1

HCID 678302493Oxo-17beta-(hydroxymethyl)-4-methyl-4-androstene

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent3×

Procedure

A mixture of potassium-t-butoxide (5 g) in 100 ml t-butanol is heated to reflux. A solution of 3-oxo-17β-(hydroxymethyl)-4-androstene (10 g) in t-butanol is added followed by a solution of methyl iodide (2.7 g) in t-butanol. Heating is continued for 3 hours. The mixture is then cooled, acidified, and extracted with dichloromethane. The dichloromethane solution is washed with brine, dried, and concentrated to yield 3oxo-17β-(hydroxymethyl)-4-methyl-4-androstene.

Workup

  1. temperatureis heated to reflux
  2. temperatureHeating
  3. temperatureThe mixture is then cooled
  4. extractionextracted with dichloromethane
  5. washThe dichloromethane solution is washed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-daeaf2b01f0647c3a66a8a319af672d9
Source dataset
uspto-grants-1990_08
Patent number
US04946834

Reaction notes

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