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

HRID 1754371ノート

反応式

HRID 1754371 の反応式
[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

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178437817HCID 178437817、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-da94efa4d6144e62ba5bdb2c0534b0de
出典データセット
uspto-grants-2015_10
特許番号
US09169248B2

反応ノート

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