반응 #52276

반응 방정식

H2O

5-benzyloxyindole

sodium hydride

Ethyl-β-bromocaproate

→

title compound

수율 40.0%

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

수율 40.0%

용매

DMF

DMF

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction was stirred at room temperature overnight
2. 2
   추출extracted with ethyl acetate (3×50 mL)
3. 3
   건조dried over magnesium sulfate
4. 4
   농축concentrated
5. 5
   기타The residue was purified by flash chromatography on silica gel (40% ethyl acetate in hexane)

실험 절차

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).

출처