반응 #7081

반응 방정식

iodoethane

oxindole

n-butyl lithium

NH4Cl

N,N,N′,N′-tetramethylethylenediamine

→

title compound

수율 2.9%

3-Ethyl-indol-2-one

수율 2.9%

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
6. 6
   기타to afford the crude product (24.5 g, 51%)
7. 7
   기타A sample (3 g) was recrystallized from EtOAc/hexane

실험 절차

A solution of oxindole (40 g, 0.3 mol) in dry THF (400 ml) under N2 was cooled to −25° C. and treated drop wise with n-butyl lithium (2.5M in hexanes, 240 ml, 0.6 mol). To the resulting solution was added N,N,N′,N′-tetramethylethylenediamine (90.4 ml, 0.6 mol). After 30 min. iodoethane (48 ml, 0.6 mol) was added and the reaction mixture was allowed to warm to RT and stirred over night. The reaction mixture was poured into 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 crude product (24.5 g, 51%). A sample (3 g) was recrystallized from EtOAc/hexane to obtain the title compound (1.4 g), m.p. 100–101° C.; 1H-NMR (DMSO-d6) δ 0.76 (t, 3H, J=7.5 Hz), 1.8–2.0 (m, 2H), 3.38 (t, 3H, J=5.7 Hz), 6.8 (dt, 1H, J=7.69, 0.45 Hz), 6.93 (dt, 1H, J=7.45, 1.10 Hz), 7.15 (m, 1H), 7.22 (m, 1H), 10.3 (s, 1H); MS (ESI) m/z 270 [M+H].

출처