반응 #44917

반응 방정식

NaOH

2-Methyl-2,3-dihydro-benzoisothiazole

ethyl acetate methanol triethylamine

indole

Tricloroacetic acid

→

[2-(1H-Indol-3-ylsulfanyl)benzyl]methyl amine

수율 67.0%

용매

THF

ethyl acetate

반응 조건

후처리

1. 1
   추출Extraction
2. 2
   기타with ethyl acetate (2×10 mL) and purification by flash chromatography on silica gel (eluent

실험 절차

2-Methyl-2,3-dihydro-benzoisothiazole (VI) (Hoffmann, R. W.; Goldman, S. Chem. Ber. 111, 1978, 2716-2725) (75 mg, 0.50 mmol) was dissolved in THF (1 mL) and added to indole (V) (140 mg, 0.60 mmol) under Ar. Tricloroacetic acid (90 mg, 0.55 mmol) was added and the reaction mixture was stirred at room temperature for 16 hours. 2 mL 1N NaOH (aq) was added. Extraction with ethyl acetate (2×10 mL) and purification by flash chromatography on silica gel (eluent: ethyl acetate then ethyl acetate/methanol/triethylamine) gave 88 mg [2-(1H-Indol-3-ylsulfanyl)benzyl]methyl amine (67% yield).

출처