[2-(1H-Pyrrol-1-yl)phenyl]methanol

Synthesis

78540-08-6

61034-86-4

General procedure for the synthesis of 2-(1H-pyrrol-1-yl)benzylethanol from ethyl 2-pyrrol-1-yl-benzoate: ethyl 2-pyrrol-1-yl-benzoate (22.2 g, 103 mmol) was dissolved in toluene (140 mL), stirred and heated to 35 °C. To this solution was slowly added a toluene solution of sodium bis(2-ethoxymethoxy)hydroaluminum (70 wt%, 32 mL, 115 mmol) while maintaining the reaction temperature at 45 °C. After addition, the reaction was continued with stirring at 45°C for 1 hour. Upon completion of the reaction, the mixture was cooled to 0 °C and the reaction was quenched by careful and slow addition of 4N HCl aqueous solution (75 mL). The organic layer was separated, washed with saturated sodium bicarbonate solution (75 mL) and dried over anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to afford the target product 2-(1H-pyrrol-1-yl)benzylethanol (16.8 g, 97 mmol) as a pale yellow oil in 94% yield. Thin layer chromatography (TLC) showed Rf = 0.56 (Expander: dichloromethane/methanol = 97:3).

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