Potassium Bicarbonate → 21-Chloro-17-hydroxy-4-pregnene-3,20-dione

HRID 247537Notes

Reaction equation

HRID 247537 reaction equation
[Cl: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])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.C(=O)(O)[O-].[K+]>CO.O>[Cl: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])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 516893Potassium BicarbonateHCID 1360479021-Chloro-17-formyloxy-4-pregnene-3,20-dione

Product 1

HCID 1013341321-Chloro-17-hydroxy-4-pregnene-3,20-dioneYield 87.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

At room temperature, 1.6 g of 21-chloro-17-formyloxy-4-pregnene-3,20-dione is stirred in a mixture of 60 ml of methanol and 9 ml of water with 500 mg of potassium bicarbonate. After one hour, the reaction mixture is stirred into ice water. The thus-precipitated product is suctioned off, washed with water, and dried over sodium sulfate, yielding 1.3 g of 21-chloro-17-hydroxy-4-pregnene-3,20-dione; mp 239.4° C.

Workup

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

Sources & evidence

ORD record
ord-30d909894f6f48bebbf10476f03bbbe2
Source dataset
uspto-grants-1987_11
Patent number
US04708823

Reaction notes

Loading…