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

HRID 1196940Notes

Reaction equation

HRID 1196940 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-d9b0338e36fb46c6a526f8607780570b
Source dataset
uspto-grants-1992_05
Patent number
US05116844

Reaction notes

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