1,3-Dichloroacetone → 4-(Chloromethyl)-2-(4-fluorophenyl)-1,3-oxazole
Reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.[Cl:11][CH2:12][C:13]([CH2:15]Cl)=O>C(O)C>[Cl:11][CH2:12][C:13]1[N:8]=[C:6]([C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)[O:7][CH:15]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4-Fluorobenzamide (10.0 g) and 1,3-dichloroacetone (9.5 g) were dissolved in ethanol (100 mL), and the mixture was refluxed for 8 hr. After cooling, the reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=10:1 to 7:1) to give the title compound (4.3 g) as a white solid.
Workup
- temperaturethe mixture was refluxed for 8 hr
- temperatureAfter cooling
- concentrationthe reaction mixture was concentrated under reduced pressure
- customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=10:1 to 7:1)
Sources & evidence
- ORD record
- ord-db2488b11fbc417f86b2ac50312a961a
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08026370B2
Reaction notes
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