Potassium Bicarbonate → HCID 53908225, compound

HRID 1285291Notes

Reaction equation

HRID 1285291 reaction equation
[Br:1][CH2:2][C:3](=[O:27])[C@:4]1([O:24]C=O)[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH:14]=[CH:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.C(=O)(O)[O-].[K+]>CO.O.C(OCC)(=O)C>[Br:1][CH2:2][C:3](=[O:27])[C@:4]1([OH:24])[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH:14]=[CH:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1

Participants

6

Reactant 2

HCID 516893Potassium BicarbonateHCID 56608473HCID 56608473, compound

Product 1

HCID 53908225HCID 53908225, compoundYield 85.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under argon, 4.0 g of 21-bromo-17-formyloxy-1,4-pregnadiene-3,20-dione is agitated in a mixture of 150 ml of methanol and 24 ml of water with 1.3 g of potassium bicarbonate at room temperature. After one hour, the reaction mixture is introduced into ice water, the precipitated product is suctioned off, dissolved in ethyl acetate, washed with water, and dried over sodium sulfate, yielding 3.2 g of 21-bromo-17-hydroxy-1,4-pregnadiene-3,20-dione, mp 189.9° C. (decomposition).

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-701ff8d8976d427c82d275f2d3c9fe9a
Source dataset
uspto-grants-1986_01
Patent number
US04567002

Reaction notes

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