تفاعل #9414

معادلة التفاعل

oxindole

n-butyllithium

1,4-diiodobutane

N,N,N′,N′-tetramethylethylenediamine

→

subtitled compound

المردود 50.0%

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

المردود 50.0%

المذيبات

THF

water

THF

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with EtOAc (×2)
2. 2
   غسيلthe combined organic layers were washed with dilute HCl (pH 1) and water (×2)
3. 3
   تجفيفdried (MgSO4)
4. 4
   أخرىevaporated
5. 5
   أخرىThe residue was purified by column chromatography (SiO2, EtOAc:hexane 1:4)

الإجراء التجريبي

To a −25° C. solution of oxindole (2.0 g, 15.0 mmol) in 40 (cm3) of anhydrous THF under N2 was added n-butyllithium (1.6 M in hexanes, 19.7 cm3, 31.5 mmol) drop-wise. To the resulting milky solution was added N,N,N′,N′-tetramethylethylenediamine (4.75 cm3, 31.5 mmol). After 30 min. a solution of 1,4-diiodobutane (21.9 g, 70.6 mmol) in THF (3 cm3) was added and the reaction mixture was allowed to warm to RT and stirred for 14 h. The reaction mixture was poured into water, extracted with EtOAc (×2), the combined organic layers were washed with dilute HCl (pH 1) and water (×2), dried (MgSO4) and evaporated. The residue was purified by column chromatography (SiO2, EtOAc:hexane 1:4) to afford the subtitled compound (1.4 g, 7.5 mmol, 50%) as a tan solid: 1H NMR (CDCl3) δ 1.8–2.2 (m, 8H), 6.94 (dd, J=7.5, 1.0 Hz, 1H), 7.01 (dd, J=7.5, 1.0 Hz, 1H), 7.14–7.25 (m, 2H), 9.30 (br s, 1H).

المصدر