Synthesis
At 0 °C and under nitrogen protection, n-butyllithium (83.0 mL, 133 mmol, 1.6 M hexane solution) was slowly added dropwise to a stirred solution of 2-methylfuran (10.0 mL, 111 mmol) in tetrahydrofuran (85 mL). The reaction mixture was stirred at room temperature for 4 hours and then cooled to 0°C again. Subsequently, ethylene oxide (8.30 mL, 166 mmol) was added slowly and the reaction mixture was gradually warmed to room temperature over 16 hours. Upon completion of the reaction, the reaction was quenched by the addition of saturated aqueous ammonium chloride, the organic layer was separated, and the aqueous layer was extracted with ether (2 x 250 mL). The organic layers were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure. Finally, purification by atmospheric pressure distillation (boiling point 170-185 °C) gave 10.1 g (80.3 mmol, 72% yield) of the target product 2-(5-methylfuran-2-yl)ethanol as a light yellow oil.
References
[1] Patent: WO2009/3077, 2008, A1. Location in patent: Page/Page column 66
[2] Advanced Synthesis and Catalysis, 2006, vol. 348, # 16-17, p. 2501 - 2508
[3] Tetrahedron, 2009, vol. 65, # 44, p. 9021 - 9029
[4] Patent: US2002/173445, 2002, A1
[5] Patent: US2004/77605, 2004, A1
