Synthesis
General procedure for the synthesis of 3-(hydroxymethyl)pyrazole from 1H-pyrazole-3-carboxylic acid: a tetrahydrofuran solution (20 mL) of aluminum (III) hydride was cooled to 0 °C under nitrogen protection and stirred. To this solution was added 1H-pyrazole-3-carboxylic acid (4 g, 35.7 mmol). The reaction mixture was stirred at room temperature for 1 hour and then heated to reflux overnight. Upon completion of the reaction, the mixture was cooled to 0 °C and water (2.7 mL), 10% NaOH solution (5.4 mL) and water (8.1 mL) were added sequentially to quench the reaction. After quenching, the mixture was continued to be stirred at 0 °C for 30 min and then filtered through a Celite pad. The filtrate was concentrated under reduced pressure to remove the solvent and the resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane, 1/2, v/v) to afford the target product (1H-pyrazol-3-yl)methanol (1.9 g, 19.37 mmol, 54% yield) as a buttery solid. m/z = 81.1 [M + H - H2O]+ was shown by LCMS detection.
References
[1] Patent: WO2017/216726, 2017, A1. Location in patent: Page/Page column 968
[2] Patent: WO2014/66795, 2014, A1. Location in patent: Paragraph 0175
