反応 #7226

反応方程式

2-chloromethylbenzimidazole

N,N-diisopropylethylamine

2-(trimethylsilyl)ethoxymethyl chloride

→

title compound

収率 67.7%

2-Chloromethyl-1-(2-trimethylsilylethoxymethyl)-1H-benzimidazole

収率 67.7%

溶媒

THF

反応条件

後処理

1. 1
   その他was removed in vacuo
2. 2
   洗浄washed with water (100 mL) and brine (100 mL)
3. 3
   乾燥The organic layer was dried over sodium sulfate
4. 4
   ろ過filtered
5. 5
   濃縮concentrated in vacuo
6. 6
   その他to afford the crude product as a yellow oil
7. 7
   その他Purification by flash chromatography (silica gel, 100:2:1 CH2Cl2-methanol-ammonium hydroxide)

実験手順

To a stirred solution of 2-chloromethylbenzimidazole (1.89 g, 11.4 mmol) in dry THF (57 mL) was added N,N-diisopropylethylamine (3.00 mL, 17.2 mmol) and 2-(trimethylsilyl)ethoxymethyl chloride (1.90 mL, 10.8 mmol) both via syringe under nitrogen at room temperature. The mixture was stirred for 3 days at which time the solvent was removed in vacuo. The residue was taken up in CH2Cl2 (100 mL) and washed with water (100 mL) and brine (100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford the crude product as a yellow oil. Purification by flash chromatography (silica gel, 100:2:1 CH2Cl2-methanol-ammonium hydroxide) provided 2.17 g (65%) of the title compound as a yellow oil, which solidified on standing. 1H NMR (CDCl3) δ−0.06 (s, 9H), 0.92 (t, 2H, J=7.5 Hz), 3.57 (t, 2H, J=7.5 Hz), 4.91 (s, 2H), 5.65 (s, 2H), 7.31–7.36 (m, 2H), 7.50 (d, 1H, J=7.5 Hz), 7.78 (d, 1H, J=7.5 Hz).

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