Water → 20-Ethoxy-21-formyl-3alpha-hydroxy-5alpha-pregn-20-en-11-one

HRID 1973724Notes

Reaction equation

HRID 1973724 reaction equation
C([O:4][C@@H:5]1[CH2:28][CH2:27][C@@:26]2([CH3:29])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:25]2[C:24](=[O:30])[CH2:23][C@@:22]2([CH3:31])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15]([O:19][CH2:20][CH3:21])=[CH:16][CH:17]=[O:18])[CH2:6]1)(=O)C.C(=O)(O)[O-].[K+].O>C(O)C>[CH2:20]([O:19][C:15]([C@@H:14]1[C@:22]2([CH3:31])[C@H:11]([C@H:10]3[C@H:25]([C:24](=[O:30])[CH2:23]2)[C@:26]2([CH3:29])[C@H:7]([CH2:6][C@H:5]([OH:4])[CH2:28][CH2:27]2)[CH2:8][CH2:9]3)[CH2:12][CH2:13]1)=[CH:16][CH:17]=[O:18])[CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 516893Potassium BicarbonateHCID 867342913alpha-Acetoxy-20-ethoxy-21-formyl-5alpha-pregn-20-en-11-one

Product 1

HCID 8673429020-Ethoxy-21-formyl-3alpha-hydroxy-5alpha-pregn-20-en-11-oneYield 34.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3α-acetoxy-20-ethoxy-21-formyl-5α-pregn-20-en-11-one (500 mg) in ethyl alcohol (15 ml) was treated with potassium bicarbonate (450 mg) and the mixture was refluxed, under nitrogen, for 7 hours, then poured into water. The product was extracted with methylene chloride, and the extract washed with water, dried and evaporated. Purification of the residue (37 mg) by preparative t.l.c. and crystallisation from methyl acetate/petrol gave title compound (154 mg) m.p. 175°-178°, [α]D - 115.9°, λmax. 258 nm (ε 18,780).

Workup

  1. temperaturethe mixture was refluxed, under nitrogen, for 7 hours
  2. extractionThe product was extracted with methylene chloride
  3. washthe extract washed with water
  4. customdried
  5. customevaporated
  6. customPurification of the residue (37 mg) by preparative t.l.c
  7. customand crystallisation from methyl acetate/petrol

Sources & evidence

ORD record
ord-f65945e4ee004e68b5a645f3d27a022e
Source dataset
uspto-grants-1976_12
Patent number
US03998829

Reaction notes

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