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

HRID 1654190Notes

Reaction equation

HRID 1654190 reaction equation
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]

Participants

7

Reactant 4

HCID 679Dimethyl Sulfoxide2×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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
15 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-76e1787fb940475c8811bb4abb708bc7
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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