Reaktion #9407

Reaktionsgleichung

1,5-diiodopentane

oxindole

n-butyllithium

ammonium chloride

N,N,N′,N′-tetramethylethylenediamine

→

subtitled compound

Ausbeute 69.6%

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

Ausbeute 69.6%

Lösungsmittel

tetrahydrofuran

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   workup.WAITAfter 15 min.
3. 3
   Sonstigethe layers were separated
4. 4
   Extraktionthe aqueous phase was extracted with EtOAc (×2)
5. 5
   ExtraktionThe combined organic layers were extracted with hydrochloric acid (1N)
6. 6
   Waschenwashed with brine (500 cm3)
7. 7
   Trocknendried (MgSO4)
8. 8
   Einengenconcentrated
9. 9
   Sonstigeto obtain an oil
10. 10
    SonstigeThe oil was triturated with hexane (200 cm3) and benzene (20 cm3)
11. 11
    SonstigeThe precipitate was collected
12. 12
    Sonstigedried in vacuo

Vorschrift

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).

Quelle