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

HRID 1108042노트

반응식

HRID 1108042 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
50 °C

실험 절차

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 THF (60 ml) was added drop-wise. 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.

후처리

  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

출처 및 근거

ORD 기록
ord-5534bb5724954c86aa2f961aa3b61bcd
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06063945

반응 노트

불러오는 중…