Water → HCID 86733308, compound

HRID 1606376Notes

Reaction equation

HRID 1606376 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@H:5]3[C@:20]([CH3:22])([CH2:21][C@@H:2]12)[C@@H:19]1[C@H:8]([C@H:9]2[C@:16]([CH3:24])([CH2:17][C:18]1=[O:23])[C:12]([C:13](=[O:15])[CH3:14])=[CH:11][CH2:10]2)[CH2:7][CH2:6]3.S(=O)(=O)(O)O.[C:30](=O)(O)[O-].[K+].[OH2:35]>CO>[OH:35][C@@H:3]1[C@@H:2]([O:1][CH3:30])[CH2:21][C@@:20]2([CH3:22])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:19]2[C:18](=[O:23])[CH2:17][C@@:16]2([CH3:24])[C@H:9]3[CH2:10][CH:11]=[C:12]2[C:13](=[O:15])[CH3:14])[CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 516893Potassium BicarbonateHCID 86733293HCID 86733293, compound

Product 1

HCID 86733308HCID 86733308, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2α,3α-Epoxy-5α-pregn-16-ene-11,20-dione (500 mg.) was dissolved in methanol (25 ml.) and to the stirred solution was added concentrated sulphuric acid (0.1 ml). The solution was stirred at room temperature for 15 minutes, then 10% potassium bicarbonate solution (5 ml.) was added, and the mixture was poured into water. The precipitate was extracted into chloroform, and the extract was dried over sodium sulphate and evaporated to an oil which was recrystallised from ethyl acetate/petrol to give title compound (370 mg.) as fine white crystals, m.p. 159°-163° , [α]D + 82.0° .

Workup

  1. extractionThe precipitate was extracted into chloroform
  2. dry with materialthe extract was dried over sodium sulphate
  3. customevaporated to an oil which
  4. customwas recrystallised from ethyl acetate/petrol

Sources & evidence

ORD record
ord-9fbc9db0c43f4b14a261a56bdbc7304e
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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