تفاعل #9407

معادلة التفاعل

1,5-diiodopentane

oxindole

n-butyllithium

ammonium chloride

N,N,N′,N′-tetramethylethylenediamine

→

subtitled compound

المردود 69.6%

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 min.
3. 3
   أخرىthe layers were separated
4. 4
   استخلاصthe aqueous phase was extracted with EtOAc (×2)
5. 5
   استخلاصThe combined organic layers were extracted with hydrochloric acid (1N)
6. 6
   غسيلwashed with brine (500 cm3)
7. 7
   تجفيفdried (MgSO4)
8. 8
   تركيزconcentrated
9. 9
   أخرىto obtain an oil
10. 10
    أخرىThe oil was triturated with hexane (200 cm3) and benzene (20 cm3)
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 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).

المصدر