반응 #1351676

반응 방정식

iodoethane

3-ethylindol-2-one

n-butyllithium

NH4Cl

N,N,N′,N′-tetramethylethylenediamine

→

title product

수율 45.0%

5-(3-Chloro-phenyl)-3,3-diethyl-1,3-dihydro-indol-2-one

수율 45.0%

용매

THF

반응 조건

후처리

1. 1
   추출extracted with EtOAc (2×)
2. 2
   세척the combined organic layers were washed with dil. HCl, water, brine
3. 3
   건조dried (MgSO4)
4. 4
   농축concentrated
5. 5
   기타The residual oil was triturated with hexane

실험 절차

A solution of 3-ethylindol-2-one (16 g, 0.1 mol) in dry THF (200 ml) under N2 was cooled to −25° C. and treated drop wise with n-butyllithium (2.5M in hexanes, 80 ml, 0.2 mol). To the resulting solution was added N,N,N′,N′-tetramethylethylenediamine (30 ml, 0.2 mol). After 30 min. iodoethane (8 ml, 0.1 mol) was added and the reaction mixture was allowed to warm to RT and stirred over night. The reaction mixture was poured into an aqueous NH4Cl solution, extracted with EtOAc (2×) and the combined organic layers were washed with dil. HCl, water, brine, dried (MgSO4) and concentrated. The residual oil was triturated with hexane to afford the title product (9 g, 45%), m.p. 156-159° C.; 1H NMR (DMSO-d6) δ 10.44 (s, 1H), 7.70-7.69 (t, 1H), 7.62-7.59 (m, 1H), 7.58 (d, 1H, J=1.7 Hz), 7.53-7.50 (m, 1H), 7.45-7.41 (t, 1H), 7.36-7.35 (m, 1H), 7.34-7.33 (m, 1H), 6.91-6.89 (d, 1H, J=8.2 Hz), 1.87-1.80 (m, 2H), 1.77-1.70 (m, 2H), 0.54-0.50 (t, 6H); MS (+ESI) m/z 190 (M+H).

출처