反応式
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1.C([Li])(C)(C)C.C1C(=O)N([I:23])C(=O)C1>O1CCCC1>[I:23][C:3]1[N:2]([CH3:1])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=1参加物
反応条件
- 温度
- -78 °C
実験手順
In an oven dried nitrogen purged 3 neck 100 mL round bottom flask, 1.00 g (7.57 mmol) of 1-methylbenzimidazole in 20 mL of dry tetrahydrofuran is cooled to −78° C. 10.69 mL (18.17 mmol) of 1.7 M t-butyllithium in hexanes is added and the reaction mixture is stirred at −78° C. for 1 h. 2.55 g (11.36 mmol) of NIS in 20 mL of dry tetrahydrofuran is added. Reaction is removed from bath and stirred at room temperature for 1 hour, quenched with saturated aqueous solution of ammonium chloride, and diluted with dichloromethane. The layers are separated, the aqueous is extracted 3×100 mL dichloromethane, dried (MgSO4), and concentrated. The crude mixture is purified by chromatography using hexanes:ethyl acetate as a solvent system. The product containing fractions are combined to obtain 0.400 g of the title compound, 21% yield. MS, ES+=259.0 (M+1); 1H NMR (DMSO-d6) δ 7.580-7.552 (m, 2H); 7.228-7.129 (m, 2H); 3.750 (s, 3H) ppm.
後処理
- customReaction
- customis removed from bath
- stirringstirred at room temperature for 1 hour
- customquenched with saturated aqueous solution of ammonium chloride
- additiondiluted with dichloromethane
- customThe layers are separated
- extractionthe aqueous is extracted 3×100 mL dichloromethane
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe crude mixture is purified by chromatography
- additionThe product containing fractions
出典と根拠
- ORDレコード
- ord-31a4aafc75154b58acd5870eecb3a0e0
- 出典データセット
- uspto-grants-2009_07
- 特許番号
- US07557103B2
関連ノート
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