Sodium hydride → 2H-Pyran, 2-[(1R)-1-[2-(2,4-difluorophenyl)oxiranyl]ethoxy]tetrahydro-

HRID 1654183노트

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HRID 1654183 반응식
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[F:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[C:17](=[O:27])[CH:18]([O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1)[CH3:19]>CS(C)=O>[O:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH:21]1[O:20][CH:18]([C:17]1([C:11]2[CH:12]=[CH:13][C:14]([F:16])=[CH:15][C:10]=2[F:9])[CH2:4][O:27]1)[CH3:19]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 108693411-Propanone, 1-(2,4-difluorophenyl)-2-[(tetrahydro-2H-pyran-2-YL)oxy]-,(2R)-

생성물 1

HCID 147064262H-Pyran, 2-[(1R)-1-[2-(2,4-difluorophenyl)oxiranyl]ethoxy]tetrahydro-수율 91.7%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

To dimethyl sulfoxide (650 ml) was added, at room temperature, 60% sodium hydride in oil (15.2 g) by portions during 10 minutes. The mixture was stirred for 10 minutes at room temperature, to which was added by portions trimethylsulfoxonium iodide (83.7 g) during one hour. To the resultant mixture was added dropwise during one hour a solution of 2',4'-difluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone (86.5 g) in dimethyl sulfoxide (150 ml). The mixture was stirred for 3 hours at room temperature, then the reaction mixture was poured into ice-water (1.5 l), which was subjected to extraction 5 times with ethyl acetate (300 ml). The ethyl acetate layer was washed with water (300 ml) for four times, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to leave 2-[1-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)ethyl]-2-(2,4-difluorophenyl)oxirane (83.4 g) as a pale yellow oily product.

후처리

  1. stirringThe mixture was stirred for 3 hours at room temperature
  2. extractionwas subjected to extraction 5 times with ethyl acetate (300 ml)
  3. washThe ethyl acetate layer was washed with water (300 ml) for four times
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-c725d848a203467fb23f9de543341426
출처 데이터셋
uspto-grants-1995_04
특허 번호
US05405861

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