Sodium hydride → HCID 9948329, compound

HRID 379657Notes

Reaction equation

HRID 379657 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[F:9][C:10]1[CH:15]=[C:14]([F:16])[C:13]([F:17])=[CH:12][C:11]=1[C:18](=[O:28])[C@H:19]([O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1)[CH3:20]>CS(C)=O>[F:9][C:10]1[CH:15]=[C:14]([F:16])[C:13]([F:17])=[CH:12][C:11]=1[C:18]1([C@H:19]([O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH3:20])[CH2:2][O:28]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 9947866HCID 9947866, compound

Product 1

HCID 9948329HCID 9948329, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Trimethylsulfoxonium iodide (697 mg, 1.2 eq) was added portionwise to a stirred mixture of sodium hydride [60% mineral oil dispersion] (122 mg, 1.15 eq) and dry dimethyl sulfoxide (7 ml) at 0° C. The resulting mixture was stirred at room temperature for 40 min and then cooled in an ice bath. A solution of (2R)-2′,4′,5′-trifluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone (760 mg) in dry dimethyl sulfoxide (2 ml) was added to the mixture and stirring was continued for 2 h at room temperature. The mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed successively with water and brine, and dried over anhydrous sodium sulfate. Evaporation of the solvent gave 2-(2,4,5-trifluorophenyl)-2-[(1R)-1-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)ethyl]oxirane ( 810 mg) as a pale yellow oil, which was a mixture of 4 diastereomers and was used for the next step without further purification.

Workup

  1. temperaturecooled in an ice bath
  2. stirringstirring
  3. waitwas continued for 2 h at room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed successively with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-a715ebc22d1d4bc288969403b44f3492
Source dataset
uspto-grants-2001_10
Patent number
US06300353B1

Reaction notes

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