Methanol → HCID 22802075, compound

HRID 2072193Notes

Reaction equation

HRID 2072193 reaction equation
[F:1][C@@H:2]1[C:21]2[C@:16]([CH3:23])([CH:17]=[CH:18][C:19](=[O:22])[CH:20]=2)[C@:15]2([F:24])[C@H:4]([C@H:5]3[C@:12]([CH3:26])([CH2:13][C@@H:14]2[OH:25])[C@@H:8]([C:9](=[O:11])[CH3:10])[C@H:7]([CH3:27])[CH2:6]3)[CH2:3]1.[Cl-].[NH4+].C[OH:31]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:1][C@@H:2]1[C:21]2[C@:16]([CH3:23])([CH:17]=[CH:18][C:19](=[O:22])[CH:20]=2)[C@:15]2([F:24])[C@H:4]([C@H:5]3[C@:12]([CH3:26])([CH2:13][C@@H:14]2[OH:25])[C@@H:8]([C:9](=[O:11])[CH:10]=[O:31])[C@H:7]([CH3:27])[CH2:6]3)[CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 70635077HCID 70635077, compound

Product 1

HCID 22802075HCID 22802075, compound

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Procedure

3.0 g. of 6α,9α-difluoro-11β-hydroxy-16α-methyl-1,4-pregnadiene-3,20-dione is dissolved in 300 ml. of methanol. After adding 1.0 g. of copper (II) acetate, air is sucked through the solution for 30 minutes and the solution is then combined with saturated ammonium chloride solution. The mixture is extracted with dichloromethane, the organic phase is washed with water and dried over sodium sulfate. After evaporating the solvent under vacuum, 3.3 g. of 6α,9α-difluoro-11β-hydroxy-3,20-dioxo-16α-methyl-1,4-pregnadien-21-al is obtained in the form of a foam.

Workup

  1. additionAfter adding 1.0 g
  2. extractionThe mixture is extracted with dichloromethane
  3. washthe organic phase is washed with water
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporating the solvent under vacuum, 3.3 g

Sources & evidence

ORD record
ord-031813debba24879868d04ea218108c1
Source dataset
uspto-grants-1977_09
Patent number
US04049804

Reaction notes

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