Water → HCID 86733312, compound

HRID 1606381Notes

Reaction equation

HRID 1606381 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]([CH3:23])([CH2:17][CH2:18]1)[C:12]([C:13](=[O:15])[CH3:14])=[CH:11][CH2:10]2)[CH2:7][CH2:6]3.S(=O)(=O)(O)O.[C:29](=O)(O)[O-:30].[K+].O>CO>[OH:1][C@@H:3]1[C@@H:2]([O:30][CH3:29])[CH2:21][C@@:20]2([CH3:22])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:19]2[CH2:18][CH2:17][C@@:16]2([CH3:23])[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 86733310HCID 86733310, compound

Product 1

HCID 86733312HCID 86733312, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2α,3α-Epoxy-5α-pregn-16-en-20-one (500 mg.) in methanol (30 ml.) was treated with concentrated sulphuric acid (0.1 ml.). The reaction solution was stirred at room temperature for 10 minutes, and then potassium bicarbonate solution (10%, 6 ml.) and water were added and the precipitate was extracted into chloroform. The chloroform solution was evaporated to an oil which was purified by preparative TLC in ethyl acetate/petrol (1/2), to give, as the major product title compound (255 mg) as colourless plates (from ethyl acetate/petrol), m.p. 186°-189°, [α]D (c, 0.82) + 62° , λmax (EtOH) 239 nm (ε 8370).

Workup

  1. extractionthe precipitate was extracted into chloroform
  2. customThe chloroform solution was evaporated to an oil which
  3. customwas purified by preparative TLC in ethyl acetate/petrol (1/2)

Sources & evidence

ORD record
ord-9ce92a2b18f440878333db98f810ed97
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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