Methanol → HCID 86733980, compound

HRID 1576353Notes

Reaction equation

HRID 1576353 reaction equation
[C:1]([O:4][C:5]1[CH:22]=[CH:21][C:20]2[C@:19]3([OH:23])[C@H:10]([C@H:11]4[C@@:15]([CH2:17][C@@H:18]3[OH:24])([CH3:16])[C:14](=[O:25])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1)(=[O:3])[CH3:2].[Cr](O)(O)(=O)=O.CO.O>CC(C)=O>[C:1]([O:4][C:5]1[CH:22]=[CH:21][C:20]2[C@:19]3([OH:23])[C@H:10]([C@H:11]4[C@@:15]([CH2:17][C:18]3=[O:24])([CH3:16])[C:14](=[O:25])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24425Chromic AcidHCID 22792566HCID 22792566, compound

Product 1

HCID 86733980HCID 86733980, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Acetoxy-9α,11β -dihydroxy-oestra-1,3,5(10)-trien-17-one (690 mg.) in acetone (30 ml) at 5° was treated dropwise with stirring with 8N chromic acid (1.0 ml). The solution was stirred for 5 mins. then methanol (1 ml), and water (30 ml) were added. The organic solvents were distilled off in vacuo and the steroid extracted into ethyl acetate. The organic solution was washed with dilute hydrochloric acid, then water, dried and the solvent was evaporated. The resulting gum was crystallised from methanol to give the title compound (247 mg, 36%), m.p. 247°-8°, [α]D + 297° (c. 1.0 in dioxan).

Workup

  1. distillationThe organic solvents were distilled off in vacuo
  2. extractionthe steroid extracted into ethyl acetate
  3. washThe organic solution was washed with dilute hydrochloric acid
  4. dry with materialwater, dried
  5. customthe solvent was evaporated
  6. customThe resulting gum was crystallised from methanol

Sources & evidence

ORD record
ord-09ca7f1a15e54ce38054e0d7ff384f74
Source dataset
uspto-grants-1976_09
Patent number
US03980681

Reaction notes

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