反応 #607476

反応方程式

2

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

NaH

bromoacetonitrile

→

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

収率 55.0%

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

収率 55.0%

溶媒

DMF

反応条件

後処理

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

実験手順

A 125-mL single-neck round-bottomed flask equipped with a magnetic stirrer and nitrogen inlet was purged with nitrogen and charged with 2 (5.76 g, 29.8 mmol) and DMF (50 mL). The solution was cooled to 0° C. using an ice bath. 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 ethyl 1-(cyanomethyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylate 3 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)

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