Methanol → 6-Chloro-11beta,21-dihydroxy-16alpha-methyl-4,6-pregnadiene-3,20-dione

HRID 2049150Notes

Reaction equation

HRID 2049150 reaction equation
C([O:4][CH2:5][C:6](=[O:30])[C@@H:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([C@@H:22]([OH:26])[CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:27])[CH2:17][CH2:18]2)[C:13]([Cl:28])=[CH:12]3)[CH2:9][C@H:8]1[CH3:29])(=O)C.CO.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C>[Cl:28][C:13]1[C:14]2[C@:19]([CH3:20])([CH2:18][CH2:17][C:16](=[O:27])[CH:15]=2)[C@@H:21]2[C@H:11]([C@H:10]3[C@:24]([CH3:25])([CH2:23][C@@H:22]2[OH:26])[C@@H:7]([C:6](=[O:30])[CH2:5][OH:4])[C@H:8]([CH3:29])[CH2:9]3)[CH:12]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 7058539321-Acetoxy-6-chloro-11beta-hydroxy-16alpha-methyl-4,6-pregnadiene-3,20-dione

Product 1

HCID 705844446-Chloro-11beta,21-dihydroxy-16alpha-methyl-4,6-pregnadiene-3,20-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2.95 g. of 21-acetoxy-6-chloro-11β-hydroxy-16α-methyl-4,6-pregnadiene-3,20-dione in 80 ml. of methanol is combined with 800 mg. of potassium carbonate and stirred for 5 minutes at room temperature under argon. After adding 5 ml. of acetic acid and 5 ml. of water, the reaction solution is completely evaporated under vacuum. The residue is chromatographed on silica gel. With 42-50% acetone-hexane and after recrystallization from acetone-diisopropyl ether, 1.55 g. of 6-chloro-11β,21-dihydroxy-16α-methyl-4,6-pregnadiene-3,20-dione is obtained, m.p. 229° [α]D25 =+175° (methanol). UV: ε285 =19,850 (methanol).

Workup

  1. additionAfter adding 5 ml
  2. customof water, the reaction solution is completely evaporated under vacuum
  3. customThe residue is chromatographed on silica gel
  4. customWith 42-50% acetone-hexane and after recrystallization from acetone-diisopropyl ether, 1.55 g

Sources & evidence

ORD record
ord-8ab837f14d4b4ee2b052a0d4272dbfc2
Source dataset
uspto-grants-1980_04
Patent number
US04196203

Reaction notes

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