Synthesis
General procedure for the synthesis of 2-hydroxymethylthiazole from 2-formylthiazole: Thiazole-2-carbaldehyde (301 mg, 2.66 mmol) was dissolved in methanol (15 mL) at 0 °C. Subsequently, sodium borohydride (151 mg, 3.99 mmol) was slowly added to the reaction system and the reaction was continuously stirred for 2 h at this temperature. Upon completion of the reaction, the reaction mixture was poured into water (10 mL) to terminate the reaction. The solvent was removed by rotary evaporator and the resulting residue was extracted with ethyl acetate (15 mL x 3). The organic phases were combined, washed with saturated saline (15 mL) and dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed by concentration under reduced pressure, and the crude product obtained was purified by column chromatography (eluent: petroleum ether/ethyl acetate, 5:1, v/v/v/v), and finally 285 mg of a light yellow oily product was obtained with a yield of 93%.
References
[1] Chinese Journal of Chemistry, 2014, vol. 32, # 6, p. 538 - 544
[2] Patent: CN106749268, 2017, A. Location in patent: Paragraph 0798; 0799
[3] European Journal of Organic Chemistry, 2017, vol. 2017, # 33, p. 4972 - 4983
[4] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2007, vol. 62, # 12, p. 1525 - 1529
[5] Tetrahedron, 1988, vol. 44, # 7, p. 2021 - 2032
