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

HRID 1654190ノート

反応式

HRID 1654190 の反応式
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]

参加物

7

反応物 4

HCID 679Dimethyl Sulfoxide2 回HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 10265121(2S)-1-(2,4-Difluorophenyl)-2-((tetrahydro-2H-pyran-2-yl)oxy)propan-1-one

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
15 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-76e1787fb940475c8811bb4abb708bc7
出典データセット
uspto-grants-1995_04
特許番号
US05405861

反応ノート

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