Pinacol → 5-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(tris(propan-2-yl)silyl)-1,3-oxazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(triisopropylsilyl)oxazole (6.7 g) in THF (200 mL) was added dropwise n-butyllithium hexane solution (1.6M, 22.3 mL) at −78° C. The reaction mixture was stirred at −78° C. for 1 hr under nitrogen atmosphere, triisopropylborate (8.2 mL) was added thereto, and mixture was stirred at −78° C. for 2 hr. The mixture was allowed to be warmed to room temperature, and stirred overnight. To the reaction mixture was added a solution of 2,3-dimethylbutane-2,3-diol (3.51 g) in THF (20 mL) and acetic acid (2.3 mL), and the mixture was stirred at room temperature for 2 hr. The solvent was evaporated under reduced pressure, water was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (8.8 g).

Provenance & Evidence