Water → HCID 13823827, compound

HRID 1285293Notes

Reaction equation

HRID 1285293 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:18](=[CH: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.O.C(=O)(O)[O-].[K+].[Cl-].[Na+]>CO>[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:18](=[CH: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

6

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 516893Potassium BicarbonateHCID 18601432HCID 18601432, compound

Product 1

HCID 13823827HCID 13823827, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.5 g of 21-bromo-17-formyloxy-4,9(11)-pregnadiene-3,20-dione is stirred at room temperature under argon in 100 ml of methanol and 18 ml of water with 1.3 g of potassium bicarbonate. After 45 minutes, the reaction mixture is introduced into ice water which contains sodium chloride, the thus-precipitated product is suctioned off, washed repeatedly with water, and dried under vacuum, thus obtaining 2.2 g of 21-bromo-17-hydroxy-4,9(11)-pregnadiene-3,20-dione [J. Org. Chem. 44 : 1582 (1979)]in the form of a crude product which is stirred in 50 ml of acetone and 2.7 g of potassium acetate at 50° C. After 2 hours, the reaction mixture is stirred into ice water, the thus-precipitated product is suctioned off, dissolved in ethyl acetate, washed with water, and dried over sodium sulfate, thus obtaining 1.9 g of 21-acetoxy-17-hydroxy-4,9(11)-pregnadiene-3,20-dione, mp 235.8° C.

Workup

  1. washwashed repeatedly with water
  2. customdried under vacuum

Sources & evidence

ORD record
ord-cd162867ee514a5c91d57de89053b9c4
Source dataset
uspto-grants-1986_01
Patent number
US04567002

Reaction notes

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