Water → 2-(((Tert-butyldimethylsilyl)oxy)methyl)prop-2-en-1-ol

Participants

Reaction Steps

To a dry flask containing sodium hydride (2.270 g, 56.75 mmol) in THF (150 mL) under N2 at 0° C. was added slowly 2-methylenepropane-1,3-diol (5 g, 56.75 mmol). The reaction was warmed to room temperature and stirred 45 min. TBS-Cl (8.55 g, 56.75 mmol) was added in one batch and stirring was continued for another 45 min, until complete by TLC. To the reaction was added water and the mixture was extracted three times with EtOAc and washed with brine. The organics were dried over magnesium sulfate, filtered and concentrated at −10-15° C. Silica gel chromatography (20%-50% EtOAc/Hex) afforded the title compound (11.36 g, 99%) as a clear oil.

Provenance & Evidence