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

HRID 365453

反応式

HRID 365453 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
55 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3e5c83623dbe4e958dfd751ade8d27a0
出典データセット
uspto-grants-2000_10
特許番号
US06127366

関連ノート

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