Реакция #7093

Уравнение реакции

1,5-diiodopentane

oxindole

n-butyllithium

ammonium chloride

N,N,N′,N′-tetramethylethylenediamine

→

subtitled compound

Выход 69.6%

Spiro[cyclohexane-1,3′-[3H]indol]-2′-(1′H)one

Выход 69.6%

Растворители

tetrahydrofuran

EtOAc

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added
2. 2
   ДругоеAfter 15 min. the layers were separated
3. 3
   Экстракцияthe aqueous phase was extracted EtOAc (×2)
4. 4
   ЭкстракцияThe combined organic layers were extracted with hydrochloric acid (1N)
5. 5
   Промывкаwashed with brine (500 cm3)
6. 6
   Сушкаdried (MgSO4)
7. 7
   Концентрированиеconcentrated
8. 8
   Другоеto obtain an oil
9. 9
   ДругоеThe oil was triturated with hexane (200 cm3) and benzene (20 cm3)
10. 10
    ДругоеThe precipitate was collected
11. 11
    Другоеdried in vacuo

Методика

A solution of oxindole (25 g, 0.19 mol) in anhydrous tetrahydrofuran (800 cm3) was cooled to −20° C., then n-butyllithium (2.5M in hexanes, 152 cm3, 0.38 mol) was added slowly followed by N,N,N′,N′-tetramethylethylenediamine (51 cm3, 0.38 mol,). After 15 min. 1,5-diiodopentane (174 g, 0.54 mol) was added slowly and the mixture was allowed to warm to room temperature. After stirring for 16 h. saturated aqueous ammonium chloride solution (1 L) and EtOAc (1 L) were added. After 15 min. the layers were separated and the aqueous phase was extracted EtOAc (×2). The combined organic layers were extracted with hydrochloric acid (1N), then washed with brine (500 cm3), dried (MgSO4), and concentrated to obtain an oil. The oil was triturated with hexane (200 cm3) and benzene (20 cm3). The precipitate was collected and dried in vacuo to obtain the subtitled compound (26.3 g, 69.6%) as colorless crystals: mp 110–114° C.; 1H NMR (DMSO-d6) δ 1.67 (m, 10H), 6.84 (d, 1H, J=8 Hz) 6.94 (t, 1H, J=8 Hz), 7.17 (t, 1H, J=8 Hz), 7.44 (d, 1H, J=8 Hz), 10.3 (s, 1H).

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