Methanol → HCID 70561763、化合物

HRID 1076280ノート

反応式

HRID 1076280 の反応式
[F:1][C@:2]12[C@@H:22]([OH:23])[CH2:21][C@@:20]3([CH3:24])[C@@H:12]([CH2:13][C@@H:14]([CH3:25])[C@@H:15]3[C:16](=[O:19])[CH2:17][OH:18])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:27])[CH:4]=[CH:5][C:6](=[O:26])[CH:7]=1.C[OH:29]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(Cl)Cl>[F:1][C@:2]12[C@@H:22]([OH:23])[CH2:21][C@@:20]3([CH3:24])[C@@H:12]([CH2:13][C@@H:14]([CH3:25])[C@@H:15]3[C:16](=[O:19])[C:17]([OH:29])=[O:18])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:27])[CH:4]=[CH:5][C:6](=[O:26])[CH:7]=1

参加物

5

反応物 2

HCID 887Methanol2 回HCID 5311067Desoximetasone

生成物 1

HCID 70561763HCID 70561763、化合物

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

One gram of 9α-fluoro-11β,21-dihydroxy-16α-methyl-1.4-pregnadiene-3,20-dione is dissolved in 125 ml. of methanol and combined with a solution of 250 mg. of copper(II) acetate in 125 ml. of methanol. The mixture is stirred for 15 minutes at room temperature while passing air therethrough, and then is combined with methylene chloride, washed with 5% ammonium chloride solution and water, and concentrated under vacuum. The thus-obtained product is dissolved in 50 ml. of methanol. The solution is mixed with 165 mg. of potassium cyanide, 1.0 ml. of acetic acid, and 5 g. of manganese(IV) oxide and agitated for 30 minutes at room temperature. Then the mixture is filtered, the filtrate diluted with methylene chloride, washed with water, dried, and concentrated under vacuum. The residue is chromatographed over a silica gel column, recrystallized from acetone/hexane, and the methyl ester of 9α-fluoro-11β-hydroxy-3,20-dioxo-16α-methyl-1,4-pregnadiene-21-oic acid is thus produced, m.p. 215° C.

後処理

  1. washwashed with 5% ammonium chloride solution and water
  2. concentrationconcentrated under vacuum
  3. dissolutionThe thus-obtained product is dissolved in 50 ml
  4. additionThe solution is mixed with 165 mg
  5. stirringof manganese(IV) oxide and agitated for 30 minutes at room temperature
  6. filtrationThen the mixture is filtered
  7. additionthe filtrate diluted with methylene chloride
  8. washwashed with water
  9. customdried
  10. concentrationconcentrated under vacuum
  11. customThe residue is chromatographed over a silica gel column
  12. customrecrystallized from acetone/hexane

出典と根拠

ORDレコード
ord-8d41a99ce9f448298db02ad27e127564
出典データセット
uspto-grants-1976_05
特許番号
US03956347

反応ノート

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