Tetrahydrofuran → 2-(2,4-Difluorophenyl)-2-[1-(pyridin-3-yl)ethyl]oxirane

HRID 2380055Notes

Reaction equation

HRID 2380055 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:18])[CH:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[CH3:11].O1CCC[CH2:20]1>O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH:10]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH3:11])[CH2:20][O:18]1

Participants

4

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 189565411-(2,4-Difluorophenyl)-2-(pyridin-3-yl)propan-1-one

Product 1

HCID 189565362-(2,4-Difluorophenyl)-2-[1-(pyridin-3-yl)ethyl]oxirane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of dimethylsulphoxonium methylide (36.5 ml of a 0.6M solution in tetrahydrofuran) was added dropwise to a stirred solution of the product of part (ii) (4.36 g) in tetrahydrofuran (35 ml) at -20°. The solution was allowed to warm to room temperature and stirring was continued for 18 hours and then diluted with water. The mixture was extracted with ethyl acetate and the combined extracts were dried (Na2SO4). Evaporation of the solvent gave the title compound as an oil (4.50 g) which was used directly in the next stage.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialthe combined extracts were dried (Na2SO4)
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-dda4588133a049e2b524c2b4358c2a79
Source dataset
uspto-grants-1994_11
Patent number
US05364938

Reaction notes

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