反応 #52276

反応方程式

H2O

5-benzyloxyindole

sodium hydride

Ethyl-β-bromocaproate

→

title compound

収率 40.0%

3-(5-Benzyloxy-indol-1-yl)-hexanoic acid ethyl ester

収率 40.0%

溶媒

DMF

DMF

DMF

反応条件

後処理

1. 1
   workup.STIRRINGthe reaction was stirred at room temperature overnight
2. 2
   抽出extracted with ethyl acetate (3×50 mL)
3. 3
   乾燥dried over magnesium sulfate
4. 4
   濃縮concentrated
5. 5
   その他The residue was purified by flash chromatography on silica gel (40% ethyl acetate in hexane)

実験手順

A solution of 5-benzyloxyindole (5.00 g, 22.4 mmol) in DMF (20 mL) was added dropwise to a stirred solution of sodium hydride (0.91 g, 38.1 mmol) in DMF (50 mL) at 0° C. and stirred for 20 minutes. Ethyl-β-bromocaproate (5.59 g, 26.9 mmol) in DMF (20 mL) was added and the reaction was stirred at room temperature overnight. The reaction was then poured into cold H2O (150 mL) and extracted with ethyl acetate (3×50 mL), dried over magnesium sulfate and concentrated. The residue was purified by flash chromatography on silica gel (40% ethyl acetate in hexane) to give the title compound as oil (40% yield). 1H NMR (CDCl3) δ 7.47 (d, 2H, J=7.2 Hz), 7.38 (t, 2H, J=7.1 Hz), 7.32 (d, 2H, J=8.8 Hz), 7.12 (dd, 2H, J=2.4, 13.7 Hz), 6.94 (dd, 1H, J=2.4, 10.2 Hz), 6.44 (d, 1H, J=3.1 Hz), 5.09 (s, 2H), 4.79 (m, 1H), 3.98 (q, 2H, J=7.1 Hz), 2.80 (m, 2H), 1.90 (m, 2H), 1.25 (m, 2H), 1.07 (t, 3H, J=7.2 Hz), 0.86 (t, 3H, J=7.3 Hz).

出典