Sodium hydride → 2-(3-chlorophenyl)-2-phenylOxirane

HRID 365453

반응식

HRID 365453 반응식
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[Cl:9][C:10]1[CH:11]=[C:12]([CH:21]=[CH:22][CH:23]=1)[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14]>CS(C)=O>[Cl:9][C:10]1[CH:11]=[C:12]([C:13]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:4][O:14]2)[CH:21]=[CH:22][CH:23]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 660983-ChlorobenzophenoneHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)

생성물 1

HCID 125490722-(3-chlorophenyl)-2-phenylOxirane

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
55 °C

실험 절차

A 250 mL-round bottom flask was charged with NaH (60% dispersion in mineral oil) (1.92 g, 0.048 mol), washed with petroleum ether, then treated with dry DMSO (40 mL) under N2. To this reaction mixture was added trimethylsulfoxonium iodide (10.56 g, 0.048 mol) through a solid addition funnel over 15 min. After stirring for 0.5 hr, a solution of 3-chlorobenzophenone (8.66 g, 0.04 mol) in DMSO (15 mL) was added dropwise, and the mixture was heated at 55° C. for 2 hr. The mixture was added to ice-water, extracted with ether (3×100 mL), the organics combined, dried (MgSO4), filtered, and concentrated to give the title compound.

후처리

  1. washwashed with petroleum ether
  2. additiontreated with dry DMSO (40 mL) under N2
  3. additionthrough a solid addition funnel over 15 min
  4. extractionextracted with ether (3×100 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3e5c83623dbe4e958dfd751ade8d27a0
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06127366

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