Potassium Carbonate → HCID 86742479, compound

HRID 868172Notes

Reaction equation

HRID 868172 reaction equation
[C:1]([O:4][C@:5]1([C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@:22](Br)([C@@H:23]([OH:27])[CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:29])[CH:18]=[CH:19]2)[C@@H:14]([CH3:30])[CH2:13]3)[CH2:10][C@@H:9]1[CH3:31])[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([O:4][C@:5]1([C@:25]2([CH3:26])[C@H:11]([C@H:12]3[C@@:22]4([O:27][C@H:23]4[CH2:24]2)[C@:20]2([CH3:21])[C:15](=[CH:16][C:17](=[O:29])[CH:18]=[CH:19]2)[C@@H:14]([CH3:30])[CH2:13]3)[CH2:10][C@@H:9]1[CH3:31])[C:6](=[O:8])[CH3:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium Carbonate2×HCID 70407511HCID 70407511, compound

Product 1

HCID 86742479HCID 86742479, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 800 mg of 17α-acetoxy-9α-bromo-11β-hydroxy-6α,16β-dimethyl-1,4-pregnadiene-3,20-dione in 8 ml of acetone is stirred with 1.2 g of finely triturated potassium carbonate for 22 hours at room temperature. The potassium carbonate is suctioned off and the filtrate concentrated to dryness under vacuum. The crude product is purified on 100 g of silica gel with a hexane-ethyl acetate gradient (0-50% ethyl acetate), thus isolating 480 mg of 17α-acetoxy-9,11β-epoxy-6α,16β-dimethyl-1,4-pregnadiene-3,20-dione, mp 248°-250° C.

Workup

  1. concentrationthe filtrate concentrated to dryness under vacuum
  2. customThe crude product is purified on 100 g of silica gel with a hexane-ethyl acetate gradient (0-50% ethyl acetate)

Sources & evidence

ORD record
ord-9f44841223234081a045658420a6ecab
Source dataset
uspto-grants-1988_10
Patent number
US04777165

Reaction notes

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