1,3-Dichloroacetone → 4-Chloromethyl-2-styryl-oxazole

HRID 322257

Reaction equation

HRID 322257 reaction equation
[C:1]([NH2:11])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:12][CH2:13][C:14]([CH2:16]Cl)=O.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:12][CH2:13][C:14]1[N:11]=[C:1](/[CH:2]=[CH:3]/[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[O:10][CH:16]=1

Participants

5

Reactant 3

HCID 107931,3-DichloroacetoneHCID 11430Potassium CarbonateHCID 121352-Propenamide, 3-phenyl-

Product 1

HCID 220097524-Chloromethyl-2-styryl-oxazoleYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of cinnamamide (25.3 g) and 1,3-dichloroacetone (20.9 g) was stirred for one hour at 130° C. The reaction mixture was diluted with water, neutralized with potassium carbonate, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with diethyl ether-hexane, 4-chloromethyl-2-[(E)-2-phenylethenyl]oxazole (16.9 g, 47%) was obtained. Recrystallization from diethyl ether-hexane gave colorless needles, mp 72-73° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. washFrom the fraction eluted with diethyl ether-hexane

Sources & evidence

ORD record
ord-60507feac8c145038b96233133a1f837
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Linked notes

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