Allyl bromide → Ethyl 2-[2-methyl-4-(trifluoromethyl)-5-vinyl-imidazol-1-yl]pent-4-enoate
反応式
[CH3:1][C:2]1[N:3]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:4]([CH:11]=[CH2:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[Li+].[CH3:20][CH:21]([N-]C(C)C)[CH3:22].C(Br)C=C.[NH4+].[Cl-]>C1COCC1>[CH3:1][C:2]1[N:3]([CH:13]([CH2:22][CH:21]=[CH2:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:4]([CH:11]=[CH2:12])=[C:5]([C:7]([F:8])([F:9])[F:10])[N:6]=1参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- -78 °C
実験手順
To a cooled (−78° C.) solution of ethyl 2-[2-methyl-4-(trifluoromethyl)-5-vinyl-imidazol-1-yl]acetate (790 mg, 3.01 mmol) in THF (6 mL) under nitrogen atmosphere was added LDA (2 M, 3 mL, 6.03 mmol) drop wise. After stirring the reaction mixture at −78° C. for 15 min, allyl bromide (521 μL, 6.03 mmol) was added slowly and the reaction mixture was allowed to warm to room temperature and stirred for 2 h. A saturated NH4Cl solution (20 mL) was added to the reaction mixture at 0° C. and the mixture was then extracted with EtOAc (2×100 mL). The combined EtOAc layers were then washed with brine (50 mL), dried (MgSO4), concentrated in vacuo, and purified by flash chromatography (SiO2, 80% EtOAc/hexanes) to obtain ethyl 2-[2-methyl-4-(trifluoromethyl)-5-vinyl-imidazol-1-yl]pent-4-enoate (127 mg, 0.42 mmol, 14% yield).
後処理
- temperatureto warm to room temperature
- stirringstirred for 2 h
- extractionthe mixture was then extracted with EtOAc (2×100 mL)
- washThe combined EtOAc layers were then washed with brine (50 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- custompurified by flash chromatography (SiO2, 80% EtOAc/hexanes)
出典と根拠
- ORDレコード
- ord-a7b1afa052ef4b1a87d015ec95d3edc3
- 出典データセット
- uspto-grants-2015_10
- 特許番号
- US09169248B2
反応ノート
読み込み中…