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

HRID 1196331노트

반응식

HRID 1196331 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-90c65a0f28dc4e67a8141a4d14e46d8b
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05112998

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