Potassium Acetate → HCID 70616378, compound

HRID 372745Notes

Reaction equation

HRID 372745 reaction equation
[F:1][CH:2]([F:22])[C@:3]12[CH2:19][CH2:18][C@H:17]3[C@@H:8]([CH2:9][CH2:10][C:11]4[C@@H:16]3[CH2:15][CH2:14][C:13](=[O:20])[CH:12]=4)[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:21].C([O-])(=O)C.[K+]>CC(C)=O.S(=O)(=O)(O)O.C(OCC)(=O)C.O.O.O.[Cr]>[F:1][CH:2]([F:22])[C@:3]12[CH2:19][CH2:18][C@H:17]3[C@@H:8]([CH2:9][CH2:10][C:11]4[C@@H:16]3[CH2:15][CH2:14][C:13](=[O:20])[CH:12]=4)[C@@H:7]1[CH2:6][CH2:5][C:4]2=[O:21]

Participants

7

Reactant 2

HCID 517044Potassium AcetateHCID 57106661HCID 57106661, compound

Product 1

HCID 70616378HCID 70616378, compound

Reagents, catalysts & solvents 4

HCID 1478712182-82-0CatalystHCID 180AcetoneSolventHCID 1118Sulfuric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

310 mg of crude 18,18-difluoro-17β-hydroxy-oestr-4-en-3-one (18,18-difluoro-19-nor-testosterone) are dissolved in 40 ml of acetone and oxidised for 5 minutes at 0° C with about 1.5 equivalents of a 8 N solution of chromium-VI oxide in dilute sulphuric acid (Jones reagent). Saturated potassium acetate solution is added to the reaction mixture and the resulting mixture is diluted with ethyl acetate and the organic layer is washed with a saturated sodium chloride solution until neutral, dried and evaporated in an aspirator vacuum. The resulting residue is dissolved in a mixture of hexane/ethyl acetate (2:1) and filtered through 20 times the amount by weight of silica gel. The evaporated fractions give 18,18-difluoro-oestr-4-ene-3,17-dione, which after recrystallisation from methylene chloride/hexane melts at 186°-189° C. IR spectrum: 1745, 1670 and 1620 cm-1.

Workup

  1. washthe organic layer is washed with a saturated sodium chloride solution until neutral,
  2. customdried
  3. customevaporated in an aspirator vacuum
  4. dissolutionThe resulting residue is dissolved in a mixture of hexane/ethyl acetate (2:1)
  5. filtrationfiltered through 20 times the amount by weight of silica gel

Sources & evidence

ORD record
ord-31e54f2af1ba4b53847f6f7d0814e505
Source dataset
uspto-grants-1978_05
Patent number
US04092310

Reaction notes

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