Potassium Bicarbonate → HCID 86733326, compound

HRID 1606479Notes

Reaction equation

HRID 1606479 reaction equation
C([O:4][C@@H:5]1[CH:24]=[CH:23][C@@:22]2([CH3:25])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[C:20](=[O:26])[CH2:19][C@@:18]2([CH3:27])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=O)C.C(=O)(O)[O-].[K+]>CO>[OH:4][C@@H:5]1[CH:24]=[CH:23][C@@:22]2([CH3:25])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[C:20](=[O:26])[CH2:19][C@@:18]2([CH3:27])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1

Participants

4

Reactant 2

HCID 516893Potassium BicarbonateHCID 86733327HCID 86733327, compound

Product 1

HCID 86733326HCID 86733326, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3α-acetoxy-5α-pregn-1-ene-11,20-dione (7.9 g.) in dry methanol (225 mg.) was treated with potassium bicarbonate (8.5 g.), and the mixture was refluxed under nitrogen for 11/2 hr. The reaction mixture was concentrated in vacuo, then poured into water, and the product was extracted with methylene chloride. The extract was washed with water, dried (Na2SO4), and evaporated in vacuo. The residue (6.0 g.) was purified by preparative t.l.c. and crystallisation from methyl acetate/petroleum ether to give the title compound (1.64 g.), m.p. 119°-121°, [α]D + 56.8°.

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 11/2 hr
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionpoured into water
  4. extractionthe product was extracted with methylene chloride
  5. washThe extract was washed with water
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe residue (6.0 g.) was purified by preparative t.l.c
  9. customand crystallisation from methyl acetate/petroleum ether

Sources & evidence

ORD record
ord-83b572da353a4c3f963fa8c4f8d9bb9e
Source dataset
uspto-grants-1976_04
Patent number
US03953429

Reaction notes

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