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

HRID 322257

반응식

HRID 322257 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
130 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-60507feac8c145038b96233133a1f837
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211215B1

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