Benzene → HCID 70389336, compound

HRID 1193469Notes

Reaction equation

HRID 1193469 reaction equation
[CH2:1]1[C@@H:3]2[C:4](=[O:23])[C:5]([OH:22])=[C:6]3[C@:19]([CH3:20])([CH:2]12)[C@@H:18]1[C@H:9]([C@H:10]2[C@@:14]([CH2:16][CH2:17]1)([CH3:15])[C:13](=[O:21])[CH2:12][CH2:11]2)[CH2:8][CH2:7]3.[CH:24]1C=CC=CC=1.IC>>[CH2:1]1[C@@H:3]2[C:4](=[O:23])[C:5]([O:22][CH3:24])=[C:6]3[C@:19]([CH3:20])([CH:2]12)[C@@H:18]1[C@H:9]([C@H:10]2[C@@:14]([CH2:16][CH2:17]1)([CH3:15])[C:13](=[O:21])[CH2:12][CH2:11]2)[CH2:8][CH2:7]3

Participants

4

Reactant 3

HCID 241BenzeneHCID 6328Methyl iodideHCID 70389312HCID 70389312, compound

Product 1

HCID 70389336HCID 70389336, compoundYield 75%

Procedure

To a solution of 1,2β-methylene-4-hydroxyandrost-4-ene-3,17-dione (0.314 g, 1 mmol) in benzene (10 ml) potassium tert-butoxide (0.224 g, 2 mmol) is added and the mixture heated to reflux for 30 min. After cooling, iodomethane (0.710 g, 5 mmol) is added and the mixture boiled for further 2 hours. Then the organic solution is washed with water, dried and evaporated in vacuum. The flash column chromatography of the residue on silica gel using n-hexane/ethylacetate 60:40 affords 0.246 g (75% yield) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-f9010b9c59d74ce3989b1993292a160d
Source dataset
uspto-grants-1989_03
Patent number
US04810423

Reaction notes

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