反応 #44917

反応方程式

NaOH

2-Methyl-2,3-dihydro-benzoisothiazole

ethyl acetate methanol triethylamine

indole

Tricloroacetic acid

→

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

収率 67.0%

溶媒

THF

ethyl acetate

反応条件

後処理

1. 1
   抽出Extraction
2. 2
   その他with ethyl acetate (2×10 mL) and purification by flash chromatography on silica gel (eluent

実験手順

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).

出典