Water → HCID 10853922, compound

HRID 233506Notes

Reaction equation

HRID 233506 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH2:11][C:12](=[O:33])[C@@H:13]1[C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C@H:27]([C:28](=[O:32])[CH2:29]2)[C@:25]2([CH3:26])[C@H:20]([CH2:21][CH:22]=[CH:23][CH2:24]2)[CH2:19][CH2:18]3)[CH2:15][CH2:14]1)(=O)C.O>CO>[OH:10][CH2:11][C:12](=[O:33])[C@@H:13]1[C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C@H:27]([C:28](=[O:32])[CH2:29]2)[C@:25]2([CH3:26])[C@H:20]([CH2:21][CH:22]=[CH:23][CH2:24]2)[CH2:19][CH2:18]3)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 53989573(5alpha)-21-(Acetyloxy)pregn-2-ene-11,20-dione

Product 1

HCID 10853922HCID 10853922, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of potassium carbonate in methanol (190 ml; 0.19M) was added to a suspension of (5α)-21-(acetyloxy)pregn-2-ene-11,20-dione and its 3-ene-isomer (18.8 g) in methanol (188 ml). The resulting solution was stirred at room temperature for 30 min and poured into water (3.7 l). The mixture was extracted with dichloromethane and the organic phase was washed with water, dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel to give a mixture (3:1) (15.3 g) of (5α)-21-hydroxypregn-2-ene-11,20-dione and its 3-ene-isomer.

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. washthe organic phase was washed with water
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-9cf78d01e58f4db28c84320d4e73d7e1
Source dataset
uspto-grants-1997_01
Patent number
US05593983

Reaction notes

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