m-Chloroperbenzoic acid → 6alpha,7alpha-Diepoxypregn-4-en-3one

HRID 1196314노트

반응식

HRID 1196314 반응식
ClC1C=CC=[C:4]([C:8]([O:10]O)=O)C=1.CC1(C)CO[CH:16]([CH:19]([C@@H:21]2[C@:38]3([CH3:39])[C@H:24]([C@H:25]4[C@H:35]([CH2:36][CH2:37]3)[C@:33]3([CH3:34])[C:28](=[CH:29][C:30](=[O:41])[C@@H:31]5[O:40][C@@H:32]53)C=C4)[CH2:23][CH2:22]2)C)OC1>C(Cl)(Cl)Cl>[O:40]1[C:31]2=[C:32]3[C@:33]([CH3:34])([CH2:28][CH2:29][C:30]2=[O:41])[C@@H:35]2[C@H:25]([C@H:24]4[C@:38]([CH3:39])([CH2:37][CH2:36]2)[C@@H:21]([CH2:19][CH3:16])[CH2:22][CH2:23]4)[C@@H:4]2[O:10][C@:8]123

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 8674579720-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregna-4,6-dien-3-one

생성물 1

HCID 867457986alpha,7alpha-Diepoxypregn-4-en-3one수율 76%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

A solution of 0.664 g (3.85 mmoles) of m-chloroperbenzoic acid in 50 ml of chloroform was mixed with a solution of 0.328 g (0.769 mmole) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregna-4,6-dien-3-one in 10 ml of chloroform and the resulting mixture was stirred at room temperature for 3 days. The reaction mixture was filtered and the precipitate was washed with chloroform. The filtrate and the washings were combined, diluted with chloroform and washed successively with aqueous potassium iodide solution and aqueous sodium chloride solution. Finally the organic layer was dried over magnesium sulfate and the solvent was then distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane: 1:10, v/v) to recover 0.258 g of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α;6α,7α-diepoxypregn-4-en-3-one (yield: 76%).

후처리

  1. filtrationThe reaction mixture was filtered
  2. washthe precipitate was washed with chloroform
  3. additiondiluted with chloroform
  4. washwashed successively with aqueous potassium iodide solution and aqueous sodium chloride solution
  5. dry with materialFinally the organic layer was dried over magnesium sulfate
  6. distillationthe solvent was then distilled off under reduced pressure
  7. customThe residue was purified by silica gel chromatography (eluent
  8. customethyl acetate-hexane: 1:10, v/v) to recover 0.258 g of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α

출처 및 근거

ORD 기록
ord-a6b67676d46f4cfcadc27ac7261c0425
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05112998

반응 노트

불러오는 중…