反応 #9423

反応方程式

iodoethane

3-ethyl-indol-2-one

n-butyllithium

NH4Cl

N,N,N′,N′-tetramethylethylenediamine

→

3,3-diethylindol-2-one

収率 47.6%

溶媒

THF

反応条件

後処理

1. 1
   抽出extracted with EtOAc (2×)
2. 2
   洗浄the combined organic layers were washed with dil. HCl, water, brine
3. 3
   乾燥dried (MgSO4)
4. 4
   濃縮concentrated
5. 5
   その他The residual oil was triturated with hexane

実験手順

A solution of 3-ethyl-indol-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 3,3-diethylindol-2-one (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).

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