Dimethylformamide → Ethyl 2-[2-methyl-4-(trifluoromethyl)-5-vinyl-imidazol-1-yl]acetate

HRID 1754371노트

반응식

HRID 1754371 반응식
[CH3:1][C:2]1[NH:3][C:4]([CH:11]=[CH2:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+].[CH3:24][CH2:25][O:26][C:27]([CH2:29]Br)=[O:28]>O.C1COCC1>[CH3:1][C:2]1[N:3]([CH2:29][C:27]([O:26][CH2:25][CH3:24])=[O:28])[C:4]([CH:11]=[CH2:12])=[C:5]([C:7]([F:10])([F:8])[F:9])[N:6]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178437817HCID 178437817, 화합물

생성물 1

HCID 86724376Ethyl 2-[2-methyl-4-(trifluoromethyl)-5-vinyl-imidazol-1-yl]acetate수율 59%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-methyl-4-(trifluoromethyl)-5-vinyl-1H-imidazole (911 mg, 5.17 mmol) was added DMF (7 mL) and THF (3 mL), followed by K2CO3 (1.43 g, 10.35 mmol) and ethyl bromo acetate (687 mL, 6.2 mmol). The resulting mixture was then stirred overnight at room temperature. Water (50 mL) was added and the mixture was extracted with EtOAc (3×100 mL). The combined EtOAc layers were dried (MgSO4), concentrated in vacuo, and purified by flash chromatography (SiO2, 60% EtOAc/hexanes) to obtain the desired ethyl 2-[2-methyl-4-(trifluoromethyl)-5-vinyl-imidazol-1-yl]acetate (796 mg, 3.03 mmol, 59% yield) as a yellow oil.

후처리

  1. extractionthe mixture was extracted with EtOAc (3×100 mL)
  2. dry with materialThe combined EtOAc layers were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography (SiO2, 60% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-da94efa4d6144e62ba5bdb2c0534b0de
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169248B2

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