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

HRID 2051227Notes

Reaction equation

HRID 2051227 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 3-oxo-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-84d0aee0b1834716953a8a5a5a36c3da
Source dataset
uspto-grants-1991_05
Patent number
US05017568

Reaction notes

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