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

HRID 1584326

반응식

HRID 1584326 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 heated for one hour at 130° C. The reaction mixture was poured into water, which was neutralized with potassium carbonate, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The concentrate was purified by column chromatography on silica gel. From the fraction eluted with ether-hexane (1:5, v/v), was obtained 4-chloromethyl-2-[(E)-styryl] oxazole (16.9 g, 47%), which was recrystallized from ether-hexane to yield colorless needless, m.p.72-73° C.

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe concentrate was purified by column chromatography on silica gel
  6. washFrom the fraction eluted with ether-hexane (1:5

출처 및 근거

ORD 기록
ord-c13f1359046844c7ae845f82660227f3
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05932601

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