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

HRID 1654183Notes

Reaction equation

HRID 1654183 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c725d848a203467fb23f9de543341426
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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