Potassium Acetate → HCID 70616378、化合物

HRID 372745ノート

反応式

HRID 372745 の反応式
[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]

参加物

7

反応物 2

HCID 517044Potassium AcetateHCID 57106661HCID 57106661、化合物

生成物 1

HCID 70616378HCID 70616378、化合物

試薬・触媒・溶媒 4

HCID 14787Chromium trihydroxide触媒HCID 180Acetone溶媒HCID 1118Sulfuric Acid溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-31e54f2af1ba4b53847f6f7d0814e505
出典データセット
uspto-grants-1978_05
特許番号
US04092310

反応ノート

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