Acetone → 6alpha,7alpha-Diepoxy-3-oxopregn-4-ene-20-carbaldehyde

HRID 1196331ノート

反応式

HRID 1196331 の反応式
[O:1]1[C:19]2=[C:20]3[C@:15]([CH3:22])([CH2:16][CH2:17][C:18]2=[O:21])[C@@H:14]2[C@H:4]([C@H:5]4[C@:11]([CH3:23])([CH2:12][CH2:13]2)[C@@H:8]([CH2:9][CH3:10])[CH2:7][CH2:6]4)[C@@H:3]2[O:24][C@:2]123.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C[C:43](C)=[O:44]>>[O:1]1[C:19]2=[C:20]3[C@:15]([CH3:22])([CH2:16][CH2:17][C:18]2=[O:21])[C@@H:14]2[C@H:4]([C@H:5]4[C@:11]([CH3:23])([CH2:12][CH2:13]2)[C@@H:8]([CH:9]([CH:43]=[O:44])[CH3:10])[CH2:7][CH2:6]4)[C@@H:3]2[O:24][C@:2]123

参加物

4

反応物 3

HCID 180AcetoneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 867457986alpha,7alpha-Diepoxypregn-4-en-3one

生成物 1

HCID 867458066alpha,7alpha-Diepoxy-3-oxopregn-4-ene-20-carbaldehyde収率 55%

実験手順

In 10 ml of acetone was dissolved 44.2 mg (0.1 mmole) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α;6α,7α-diepoxypregn-4-en-3-one, followed by addition of 5 mg (0.02 mmole) of pyridinium p-toluenesulfonate. The mixture was refluxed for 2 hours. The reaction mixture thus obtained was cooled to room temperature and the solvent was distilled off under reduced pressure. The residue was diluted with methylene chloride and this methylene chloride solution was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1:5, v/v) to recover 19.6 mg of 1α,2α;6α,7α-diepoxy-3-oxopregn-4-ene-20-carbaldehyde (yield: 55%).

後処理

  1. temperatureThe mixture was refluxed for 2 hours
  2. customThe reaction mixture thus obtained
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionThe residue was diluted with methylene chloride
  5. washthis methylene chloride solution was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was then distilled off under reduced pressure
  8. customthe residue was purified by silica gel chromatography (eluent
  9. customethyl acetate-hexane=1:5, v/v) to recover 19.6 mg of 1α,2α

出典と根拠

ORDレコード
ord-90c65a0f28dc4e67a8141a4d14e46d8b
出典データセット
uspto-grants-1992_05
特許番号
US05112998

反応ノート

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