87184-99-4

110-63-4

18162-48-6

87184-99-4

To a stirred solution of 1,4-butanediol (3 mL, 33.3 mmol) in anhydrous dichloromethane (30 mL) was added imidazole (2.73 g, 66.6 mmol) at 0 °C and the mixture was stirred for 30 min. Subsequently, tert-butyldimethylchlorosilane (TBSCl, 5 g, 33.3 mmol) dissolved in dichloromethane (20 mL) was added and the mixture was stirred at room temperature for 1 hour (the progress of the reaction was monitored by TLC). Upon completion of the reaction, the reaction mixture was quenched with saturated sodium bicarbonate solution. Next, it was washed with ammonium chloride solution and extracted with dichloromethane (2 x 30 mL). The organic extracts were combined, washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. Finally, the residue was purified by column chromatography (silica gel, ethyl acetate-hexane, 2:8) to afford 4-((tert-butyldimethylsilyl)oxy)butan-1-ol (TBS ether) as a colorless slurry; yield: 6.4 g (95%).