Benzene → 4-Methoxy-6-methylenandrost-4-ene-3,17-dione

HRID 620679Notes

Reaction equation

HRID 620679 reaction equation
[OH:1][C:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C:3]=1[C:4](=[CH2:23])[CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C:10]2=[O:22].[CH:24]1C=CC=CC=1.IC>>[CH3:24][O:1][C:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C:3]=1[C:4](=[CH2:23])[CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C:10]2=[O:22]

Participants

4

Reactant 3

HCID 241BenzeneHCID 6328Methyl iodideHCID 186318864-Hydroxy-6-methylenandrost-4-ene-3,17-dione

Product 1

HCID 186318914-Methoxy-6-methylenandrost-4-ene-3,17-dioneYield 75.2%

Procedure

To a solution of 4-hydroxy-6-methylenandrost-4-ene-3,17-dione (0.315 g, 1 mmole) in benzene (10 ml) potassium tert-butoxide (0.224 g, 2 mmole) is added and the mixture heated to reflux for 30 minutes. After cooling, iodomethane (0.710 g, 5 mmole) is added and the mixture boiled for a further 2 hours. Then the organic solution is washed with water, dried and evaporated in vacuum. Flash column chromatography of the residue on silica gel using n-hexane/ethyl acetate 60:40 affords 0.247 g (75% yield) of the title compound, m.p. 196°-198° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 30 minutes
  3. temperatureAfter cooling
  4. washThen the organic solution is washed with water
  5. customdried
  6. customevaporated in vacuum

Sources & evidence

ORD record
ord-2a4c1910f78941c1b51724d1e4461bca
Source dataset
uspto-grants-1989_04
Patent number
US04822528

Reaction notes

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