Reaktion #606458

Reaktionsgleichung

bromoacetonitrile

Sodium hydride

NaH

ethyl 4,5,6,7-tetrahydro-1H-indole-2-carboxylate

Ethyl 4,5,6,7-Tetrahydro-1H-indole-2-carboxylate

→

104h

Ausbeute 55.0%

Ethyl 1-(Cyanomethyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

Ausbeute 55.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 125-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet
2. 2
   Sonstigewas purged with nitrogen
3. 3
   workup.STIRRINGThe mixture was stirred at room temperature for 14 h
4. 4
   EinengenAfter that time, the reaction mixture was concentrated under reduced pressure
5. 5
   Sonstigethe residue was partitioned between ethyl acetate (150 mL) and water (450 mL)
6. 6
   SonstigeThe organic layer was separated
7. 7
   Extraktionthe aqueous layer was extracted with ethyl acetate (3×150 mL)
8. 8
   WaschenThe combined organic layers were washed with brine
9. 9
   Trocknendried over sodium sulfate
10. 10
    Einengenconcentrated under reduced pressure
11. 11
    SonstigeThe residue was purified by column chromatography

Vorschrift

A 125-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet was purged with nitrogen and charged with ethyl 4,5,6,7-tetrahydro-1H-indole-2-carboxylate 104g (5.76 g, 29.8 mmol) and DMF (50 mL). The solution was cooled to 0° C. using an ice bath. Sodium hydride, NaH (60% dispersion in mineral oil, 1.43 g, 35.8 mmol) was added. The resulting mixture was stirred at room temperature for 1 h. After that time, bromoacetonitrile (1.43 g, 35.8 mmol) was added. The mixture was stirred at room temperature for 14 h. After that time, the reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate (150 mL) and water (450 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (3×150 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford a 55% yield (3.80 g) of 104h as a yellow semi-solid: 1H NMR (300 MHz, CDCl3) δ 6.66 (s, 1H), 5.29 (s, 2H), 4.28 (q, 2H, J=7.2 Hz), 2.62 (t, 2H, J=6.3 Hz), 2.49 (t, 2H, J=6.3 Hz), 1.92 (m, 2H), 1.75 (m, 2H), 1.33 (t, 3H, J=7.2 Hz); MS (ESI+) m/z 233.1 (M+H)

Quelle