Sodium hydride → HCID 19024387, compound

HRID 1033732Notes

Reaction equation

HRID 1033732 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[H][H].[F:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[C:19](=[O:33])[C:20]([S:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)([CH3:22])[CH3:21]>CS(C)=O.CCCCCC>[F:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[C:19]1([C:20]([S:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)([CH3:22])[CH3:21])[CH2:4][O:33]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 19024388HCID 19024388, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19024387HCID 19024387, compoundYield 67,988.102%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8058HexaneSolvent

Procedure

In 900 ml of dimethyl sulfoxide was suspended 41.2 g (1.0 mol) of 60% sodium hydride having been washed with hexane, and 226.7 g (1.0 mol) of trimethyloxosulfonium iodide was added to the suspension in divided portions with stirring under cooling with ice. After the evolution of hydrogen gas ceased, stirring was continued at room temperature for an additional 2-hour period. A solution of 193.0 g (0.57 mmol) of 1-(2,4-difluorophenyl)-2-((4-methoxyphenyl)methylthio)-2-methylpropan-1-one in 110 ml of dimethyl sulfoxide was added thereto, followed by stirring for 12 hours. The reaction mixture was poured into ice-water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried. The solvent was removed by distillation under reduced pressure. The residue was subjected to column chromatography and eluted with a mixed solvent of hexane and ethyl acetate (10:1). The solvent was removed by distillation under reduced pressure, and the residue was recrystallized from a mixed solvent of diethyl ether and hexane to obtain 135.8 g (68%) of (±)-2-(2,4-difluorophenyl)-2-(1-((4-methoxyphenyl)methylthio)-1-methylethyl)oxirane as a colorless crystal.

Workup

  1. additionwas added to the suspension in divided portions
  2. temperatureunder cooling with ice
  3. stirringstirring
  4. waitwas continued at room temperature for an additional 2-hour period
  5. stirringby stirring for 12 hours
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  8. customdried
  9. customThe solvent was removed by distillation under reduced pressure
  10. washeluted with a mixed solvent of hexane and ethyl acetate (10:1)
  11. customThe solvent was removed by distillation under reduced pressure
  12. customthe residue was recrystallized from a mixed solvent of diethyl ether and hexane

Sources & evidence

ORD record
ord-0a7afc8d4212458b8d4e7a855c3550f7
Source dataset
uspto-grants-1994_05
Patent number
US05312815

Reaction notes

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