Dimethyl Sulfoxide → 1-(2-Acetoxyethyl)thio-2-(2,4-difluorophenyl)-1,1-difluoro-2,3-epoxypropane

HRID 1585661ノート

反応式

HRID 1585661 の反応式
[H-].[Na+].[CH3:3]S(C)=O.[I-].C[S+](C)(C)=O.[C:13]([O:16][CH2:17][CH2:18][S:19][C:20]([F:32])([F:31])[C:21]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[F:30])=[O:22])(=[O:15])[CH3:14]>C1COCC1>[C:13]([O:16][CH2:17][CH2:18][S:19][C:20]([F:31])([F:32])[C:21]1([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=2[F:30])[O:22][CH2:3]1)(=[O:15])[CH3:14]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 10710064HCID 10710064、化合物

生成物 1

HCID 107110891-(2-Acetoxyethyl)thio-2-(2,4-difluorophenyl)-1,1-difluoro-2,3-epoxypropane収率 90%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

A suspension of 60% NaH (3.95 g, 0.1 mol) in THF (60 ml)-DMSO (120 ml) was heated to an external temperature of 50° C., followed by the addition of trimethylsulfoxonium iodide (21.7 g, 0.1 mol) in portions. The resulting mixture was stirred for 15 minutes at the same temperature and was then cooled to -20° C. To the reaction mixture, a solution of 2-(2-acetoxyethyl)thio-2,2-difluoro-2',4'-difluoroacetophenone (25.5 g, 0.08 mol) in THE (60 ml) was added dropwise. After being stirred at room temperature for 1.5 hours, the reaction mixture was poured into ice water, followed by extraction with ethyl ether. The ether solution was washed with water, dried over magnesium sulfate and then distilled off under reduced pressure, whereby 1-(2-acetoxyethyl)thio-2-(2,4-difluorophenyl)-1,1-difluoro-2,3-epoxypropane (24.0 g, yield: 90.0%) was obtained as a pale yellow oil.

後処理

  1. temperaturewas then cooled to -20° C
  2. stirringAfter being stirred at room temperature for 1.5 hours
  3. extractionfollowed by extraction with ethyl ether
  4. washThe ether solution was washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationdistilled off under reduced pressure

出典と根拠

ORDレコード
ord-5b66a21faf3c4d109d049328ab5e2b3d
出典データセット
uspto-grants-1999_08
特許番号
US05939448

反応ノート

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