반응 #9407

반응 방정식

1,5-diiodopentane

oxindole

n-butyllithium

ammonium chloride

N,N,N′,N′-tetramethylethylenediamine

→

subtitled compound

수율 69.6%

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

수율 69.6%

용매

tetrahydrofuran

EtOAc

반응 조건

후처리

1. 1
   workup.ADDITIONwere added
2. 2
   workup.WAITAfter 15 min.
3. 3
   기타the layers were separated
4. 4
   추출the aqueous phase was extracted with EtOAc (×2)
5. 5
   추출The combined organic layers were extracted with hydrochloric acid (1N)
6. 6
   세척washed with brine (500 cm3)
7. 7
   건조dried (MgSO4)
8. 8
   농축concentrated
9. 9
   기타to obtain an oil
10. 10
    기타The oil was triturated with hexane (200 cm3) and benzene (20 cm3)
11. 11
    기타The precipitate was collected
12. 12
    기타dried in vacuo

실험 절차

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).

출처