1,3-Dichloroacetone → 4-chloromethyl-2-[(E)-2-(4-fluorophenyl)ethenyl]-1,3-oxazole

HRID 2084357Notes

Reaction equation

HRID 2084357 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([NH2:12])=[O:11])=[CH:4][CH:3]=1.[Cl:13][CH2:14][C:15]([CH2:17]Cl)=O>>[Cl:13][CH2:14][C:15]1[N:12]=[C:10](/[CH:9]=[CH:8]/[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[O:11][CH:17]=1

Participants

3

Reactant 2

HCID 107931,3-DichloroacetoneHCID 9236023-(4-Fluorophenyl)-2-propenamide

Product 1

HCID 121098664-chloromethyl-2-[(E)-2-(4-fluorophenyl)ethenyl]-1,3-oxazoleYield 43.7%

Procedure

The (E)-3-(4-fluorophenyl)-2-propenamide (17.55 g) thus obtained and 1,3-dichloroacetone (12.85 g) were molten at 130° C. and stirred for 1.5 hours. After the reaction mixture was cooled to room temperature and extracted with ethyl acetate, it was washed with ice water, saturated aqueous sodium bicarbonate, and saturated saline. After drying with anhydrous sodium sulfate, the solvent was distilled off; the residue was purified by column chromatography (eluent: diethyl ether-hexane=1:9→3:17) to yield the titled compound (10.5 g) as colorless crystals.

Workup

  1. customwere molten at 130° C.
  2. extractionextracted with ethyl acetate, it
  3. washwas washed with ice water, saturated aqueous sodium bicarbonate, and saturated saline
  4. dry with materialAfter drying with anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent: diethyl ether-hexane=1:9→3:17)

Sources & evidence

ORD record
ord-d330d255e0a541d5a747d288a0da2c2c
Source dataset
uspto-grants-2004_04
Patent number
US06716863B2

Reaction notes

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