Dimethyl Sulfoxide → 2-[(1S)-1-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)ethyl]-2-(2,4-difluorophenyl)oxirane

HRID 1654190노트

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HRID 1654190 반응식
CS(C)=O.[H-].[Na+].[I-].[CH3:8][S+](C)(C)=O.[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[C:21](=[O:31])[C@@H:22]([O:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][O:26]1)[CH3:23]>C(OCC)(=O)C.O>[O:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH:25]1[O:24][C@H:22]([C:21]1([C:15]2[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=2[F:13])[CH2:8][O:31]1)[CH3:23]

참가 물질

7

반응물 4

HCID 679Dimethyl Sulfoxide2회HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 10265121(2S)-1-(2,4-Difluorophenyl)-2-((tetrahydro-2H-pyran-2-yl)oxy)propan-1-one

생성물 1

HCID 571648292-[(1S)-1-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)ethyl]-2-(2,4-difluorophenyl)oxirane수율 76.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
15 °C

실험 절차

To dimethyl sulfoxide (5 ml) was added 60% sodium hydride in oil (85 mg), to which was added trimethyl sulfoxonium iodide (0.49 g) with stirring at about 15° C., and the mixture was stirred for 15 minutes at room temperature. The reaction mixture was cooled with ice, to which was added a dimethyl sulfoxide solution (1.2 ml) of (2S)-2',4'-difluoro-2-(3,4,5,6-tetrahydro- 2H-pyran-2-yloxy)propiophenone (0.50 g), and the mixture was stirred for two hours at room temperature. To the reaction mixture were added water (10 ml) and ethyl acetate (50 ml), and the resultant mixture was shaken. The organic layer was washed with a saturated aqueous sodium chloride solution (10 ml) twice, which was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by means of a silica gel chromatography (eluent, hexane:ethyl acetate=10:1) to afford 2-[(1S)-1-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)ethyl]-2-(2,4-difluorophenyl)oxirane (0.40 g) as a pale yellow oily product.

후처리

  1. stirringthe mixture was stirred for 15 minutes at room temperature
  2. temperatureThe reaction mixture was cooled with ice, to which
  3. stirringthe mixture was stirred for two hours at room temperature
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution (10 ml) twice
  5. dry with materialwhich was dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by means of a silica gel chromatography (eluent, hexane:ethyl acetate=10:1)

출처 및 근거

ORD 기록
ord-76e1787fb940475c8811bb4abb708bc7
출처 데이터셋
uspto-grants-1995_04
특허 번호
US05405861

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