تفاعل #531918

معادلة التفاعل

1,5-diiodopentane

oxindole

n-butyllithium

ammonium chloride

N,N,N′,N′-tetramethylethylenediamine

→

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

المردود 69.6%

المذيبات

tetrahydrofuran

EtOAc

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwere added
2. 2
   workup.WAITAfter 15 minutes
3. 3
   أخرىthe layers were separated
4. 4
   استخلاصthe aqueous phase was extracted
5. 5
   استخلاصThe combined organic layers were extracted with hydrochloric acid (1 N)
6. 6
   غسيلwashed with brine (500 mL)
7. 7
   تجفيفdried (MgSO4)
8. 8
   تركيزconcentrated
9. 9
   أخرىto obtain an oil
10. 10
    أخرىThe oil was triturated with hexane (200 mL) and benzene (20 mL)
11. 11
    أخرىThe precipitate was collected
12. 12
    أخرىdried in vacuo

الإجراء التجريبي

A solution of oxindole (25 g, 0.19 mol) in anhydrous tetrahydrofuran (800 mL) was cooled to −20° C., then n-butyllithium (2.5 M in hexanes, 152 mL, 0.38 mol) was added slowly followed by N,N,N′,N′-tetramethylethylenediamine (51 mL, 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 hours saturated aqueous ammonium chloride solution (1 L) and EtOAc (1 L) were added. After 15 minutes, the layers were separated and the aqueous phase was extracted using EtOAc (×2). The combined organic layers were extracted with hydrochloric acid (1 N), then washed with brine (500 mL), dried (MgSO4), and concentrated to obtain an oil. The oil was triturated with hexane (200 mL) and benzene (20 mL). The precipitate was collected and dried in vacuo to obtain spiro[cyclohexane-1,3′-[3H]indol]-2′-(1′H)one (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).

المصدر