反応式
C([C:5]1[NH:6][CH:7]=[CH:8][N:9]=1)CCC.CC(C)([O-])C.[K+].BrC[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[NH:6]1[CH:7]=[CH:8][N:9]=[CH:5]1.[C:19]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:18]=1参加物
実験手順
To a solution of 4.07 g (32.8 mmol) of 2-butylimidazole (obtained from step 1) in 110 mL of DMF was added 44.3 mL (44.3 mmol) of potassium tert-butoxide (1M in THF), and the resulting solution was stirred at room temperature for 15 min. To the dark brown mixture was added 20.1 g (36.1 mmol) of the bromomethyl biphenyl. The reaction mixture was stirred at room temperature for 16 h, and concentrated in vacuo. The residue was dissolved in chloroform and washed with water. The aqueous layer was extracted with fresh chloroform, and the combined extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography to give 7.2 g (37%) of the biphenyl imidazole intermediate as a yellow oil which solidified as a glass: 1H NMR (CDCl3) δ 0.90 (t, J=7.31 Hz, 3H), 1.35 (septet, J=7.5 Hz, 2H), 1.71 (quintet, J=7.74 Hz, 2H), 2.61 (t, J=7.58 Hz, 2H), 4.93 (s, 2H), 6.65 (d, J=1.35 Hz, 1H), 6.79 (d, J=8.31 Hz, 2H), 6.92 (d, J=7.3 Hz, 6H), 6.97 (d, J=1.32 Hz, 1H), 7.11 (d, J=8.2 Hz, 2H), 7.2-7.4 (m, 10H), 7.4-7.55 (m, 2H), 7.95 (dd, J=6.85, 2.08 Hz, 1H); MS(FAB) m/e (relative intensity) 607 (100, M+Li), 601 (90, M+H).
後処理
- stirringThe reaction mixture was stirred at room temperature for 16 h
- concentrationconcentrated in vacuo
- dissolutionThe residue was dissolved in chloroform
- washwashed with water
- extractionThe aqueous layer was extracted with fresh chloroform
- dry with materialthe combined extracts were dried (MgSO4)
- concentrationconcentrated in vacuo
- customThe residue was purified by chromatography
出典と根拠
- ORDレコード
- ord-154a35f741314c1f889b1e3408a6515f
- 出典データセット
- uspto-grants-1995_06
- 特許番号
- US05426105
関連ノート
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