Ethyl Acetate → 3-[3-(4,5-Diphenyloxazol-2-yl)-3-hydroxy-2-(2-hydroxyethyl)propyl]-1-(t-butyldiphenylsilyloxy)benzene

Participants

Reaction Steps

To a solution of 4,5-diphenyloxazole (5.3 g) in THF (50 ml) at -78° C. under N2 was added n-butyllithium (1.6 M in hexane, 9.2 ml). After 30 minutes, a solution of 3-(3-t-butyldiphenylsilyloxybenzyl)-2-oxotetrahydrofuran (3.3 g) in THF (30 ml) was added thereto and stirred for 1 hour at the same temperature. The reaction mixture was poured into the mixture of ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3 and brine, dried over MgSO4, and evaporated in vacuo. The oily residue was dissolved in THF (100 ml) and LiAlH4 was added to the solution at 0° C. After being stirred for 2 hours, the mixture was poured into a mixture of ethyl acetate and 1N-HCl solution. The organic layer was washed with sat. NaHCO3 and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 3-[3-(4,5-diphenyloxazol-2-yl)-3-hydroxy-2-(2-hydroxyethyl)propyl]-1-(t-butyldiphenylsilyloxy)benzene (4.3 g). MS (m/z): 654 (M+ +1) IR (Neat): 3400 cm-1NMR (CDCl3, δ): 1.09 (9H, s), 1.4-1.8 (2H, m), 2.2-2.7 (3H, m), 3.3-3.8 (2H, m), 4.6-4.8 (1H, m), 6.5-6.8 (3H, m), 6.99 (1H, t, J=8 Hz), 7.2-7.8 (20H, m)

Provenance & Evidence