Reacción #9407

Ecuación de reacción

1,5-diiodopentane

oxindole

n-butyllithium

ammonium chloride

N,N,N′,N′-tetramethylethylenediamine

→

subtitled compound

Rendimiento 69.6%

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

Rendimiento 69.6%

Disolventes

tetrahydrofuran

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added
2. 2
   workup.WAITAfter 15 min.
3. 3
   Otrothe layers were separated
4. 4
   Extracciónthe aqueous phase was extracted with EtOAc (×2)
5. 5
   ExtracciónThe combined organic layers were extracted with hydrochloric acid (1N)
6. 6
   Lavadowashed with brine (500 cm3)
7. 7
   Secadodried (MgSO4)
8. 8
   Concentraciónconcentrated
9. 9
   Otroto obtain an oil
10. 10
    OtroThe oil was triturated with hexane (200 cm3) and benzene (20 cm3)
11. 11
    OtroThe precipitate was collected
12. 12
    Otrodried in vacuo

Procedimiento

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 with 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).

Fuente