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

HRID 620678Notes

Reaction equation

HRID 620678 reaction equation
[O:1]1[C:3]23[C@:16]([CH3:21])([CH2:17][CH2:18][C:19](=[O:20])[CH:2]12)[C@@H:15]1[C@H:6]([C@H:7]2[C@@:11]([CH2:13][CH2:14]1)([CH3:12])[C:10](=[O:22])[CH2:9][CH2:8]2)[CH2:5][C:4]3=[CH2:23].[OH-].[Na+].[CH3:26]O>>[CH3:26][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 887MethanolHCID 14798Sodium HydroxideHCID 186310944,5-Epoxy-6-methylenandrostane-3,17 dione

Product 1

HCID 186318914-Methoxy-6-methylenandrost-4-ene-3,17-dioneYield 75%

Procedure

To a stirred suspension of 4,5-epoxy-6-methylenandrostane-3,17-dione (0.630 g, 2 mmole) in methanol (63 ml) is added a 4N sodium hydroxide aqueous solution (6.3 ml). The resulting mixture is refluxed for 1 hr, cooled to room temperature, evaporated in vacuo, taken up with water, neutralised with a 37% hydrochloric acid solution and kept at 0°-5° C. overnight. The resulting precipitate is filtered off, washed with water, dried and purified by flash column chromatography on silica gel eluting with n-hexane: ethyl acetate 60:40. There are obtained 0.530 g (75% yield) of the title compound, m.p. 196°-198° C.

Workup

  1. temperatureThe resulting mixture is refluxed for 1 hr
  2. customevaporated in vacuo
  3. filtrationThe resulting precipitate is filtered off
  4. washwashed with water
  5. customdried
  6. custompurified by flash column chromatography on silica gel eluting with n-hexane: ethyl acetate 60:40

Sources & evidence

ORD record
ord-2de8422c07c941348cfa27ea985a8932
Source dataset
uspto-grants-1989_04
Patent number
US04822528

Reaction notes

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