HCID 70634572, compound → HCID 70634676, compound

HRID 436364Notes

Reaction equation

HRID 436364 reaction equation
[F:1][C@@H:2]1[C:29]2[C@:24]([CH3:31])([CH:25]=[CH:26][C:27](=[O:30])[CH:28]=2)[C:23]2[C@@H:22]([OH:32])[CH2:21][C@@:20]3([CH3:33])[C@@H:5]([CH2:6][C@@H:7]([CH3:34])[C@@H:8]3[C:9](=[O:19])[CH2:10][O:11][C:12](=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:4]=2[CH2:3]1>[O-2].[Cr+6].[O-2].[O-2].CC(C)=O>[F:1][C@@H:2]1[C:29]2[C@:24]([CH3:31])([CH:25]=[CH:26][C:27](=[O:30])[CH:28]=2)[C:23]2[C:22](=[O:32])[CH2:21][C@@:20]3([CH3:33])[C@@H:5]([CH2:6][C@@H:7]([CH3:34])[C@@H:8]3[C:9](=[O:19])[CH2:10][O:11][C:12](=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:4]=2[CH2:3]1

Participants

4

Reactant 1

HCID 70634572HCID 70634572, compound

Product 1

HCID 70634676HCID 70634676, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

Procedure

300 mg. of 6α-fluoro-11β-hydroxy-21-hexanoyloxy-16α-methyl-1,4,8-pregnatriene-3,20-dione is dissolved in 7.5 ml. of acetone, combined with 0.36 ml. of a chromium (VI) oxide solution, and stirred for 1 hour at room temperature. The reaction solution is stirred into ice water; the thus-formed precipitate is vacuum-filtered and dissolved in methylene chloride. The methylene chloride solution is washed neutral, dried, and evaporated under vacuum. The crude product is purified by chromatography, and recrystallization from hexane-acetone yields 6α-fluoro-21-hexanoyloxy-16α-methyl-1,4,8-pregnatriene-3,11,20-trione, m.p. 159° C.

Workup

  1. filtrationthe thus-formed precipitate is vacuum-filtered
  2. dissolutiondissolved in methylene chloride
  3. washThe methylene chloride solution is washed neutral
  4. customdried
  5. customevaporated under vacuum
  6. customThe crude product is purified by chromatography, and recrystallization from hexane-acetone

Sources & evidence

ORD record
ord-2facb13d56794cb9ba6205b3b05cc7e6
Source dataset
uspto-grants-1977_02
Patent number
US04008313

Reaction notes

Loading…