Sodium hydride → (S)-[(3,4-Difluorophenoxy)methyl]-oxirane

HRID 1647755Notes

Reaction equation

HRID 1647755 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].[H-].[Na+].CC1C=CC(S(O[CH2:23][C@@H:24]2[CH2:26][O:25]2)(=O)=O)=CC=1>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[O:9][CH2:23][C@@H:24]1[CH2:26][O:25]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 759273,4-DifluorophenolHCID 153296Oxiranemethanol, 4-methylbenzenesulfonate, (S)-

Product 1

HCID 53482062(S)-[(3,4-Difluorophenoxy)methyl]-oxiraneYield 51.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred and cooled (ice-bath) mixture of 13.0 g of 3,4-difluorophenol and 200 ml of N,N-dimethylformamide, there were added 4.8 g of a dispersion of sodium hydride in mineral oil (50%) and, after stirring for 1 hour, a solution of 22.8 g of (S)-(oxiranylmethyl) 4-methylbenzenesulfonate (ester) in some N,N-dimethylformamide. Stirring at room temperature was continued overnight. The reaction mixture was poured into icewater and the product was extracted with methylbenzene. The extract was washed with NaCl(dil.) and water and was then dried, filtered and evaporated. The residue was distilled (13.3 Pa, 55° C.), yielding 9.5 g (51.0%)of (S)-[(3,4-difluorophenoxy)methyl]-oxirane (interm. 1).

Workup

  1. temperaturecooled
  2. stirringafter stirring for 1 hour
  3. stirringStirring at room temperature
  4. additionThe reaction mixture was poured into icewater
  5. extractionthe product was extracted with methylbenzene
  6. washThe extract was washed with NaCl(dil.) and water
  7. customwas then dried
  8. filtrationfiltered
  9. customevaporated
  10. distillationThe residue was distilled (13.3 Pa, 55° C.)

Sources & evidence

ORD record
ord-db3aaac05b3344b5a23f0f31dda8cbf9
Source dataset
uspto-grants-1995_07
Patent number
US05434168

Reaction notes

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