Synthesis
A solution of anhydrous THF (100 mL) with ethylene glycol (20.0 g, 0.322 mol) was added slowly and dropwise to an anhydrous THF (500 mL) suspension of NaH (12.9 g, 0.322 mol, 60% dispersed in mineral oil). After stirring the reaction mixture for 1 h at room temperature, tert-butyldimethylchlorosilane (TBSCl, 48.59 g, 0.322 mol) was added and stirring was continued for 1 h at room temperature. Upon completion of the reaction, the reaction was quenched with 10% aqueous K2CO3 (100 mL) and subsequently extracted with methyl tert-butyl ether (MTBE, 3 x 300 mL). The organic phases were combined, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with gradient elution using a petroleum ether solution of 1% to 33% ethyl acetate to afford 2-((tert-butyldimethylmethylsilyl)oxy)ethanol (55.0 g, 96% yield) as a colorless oil.
References
[1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 7, p. 2375 - 2385
[2] Organic Letters, 2016, vol. 18, # 18, p. 4534 - 4537
[3] Patent: US2016/122318, 2016, A1. Location in patent: Paragraph 0181
[4] Patent: WO2017/24018, 2017, A1. Location in patent: Paragraph 00131
[5] Journal of Medicinal Chemistry, 2007, vol. 50, # 9, p. 2157 - 2165
