Ethyl Acetate → 1-(Hydroxy)-1-(4,5-diphenyloxazol-2-yl)-2-(3-methoxybenzyl)cyclooctane

Participants

Reaction Steps

To a solution of 4,5-diphenyloxazole (2.1 g) in THF (30 ml) at -78° C. under N2 was added butyllithium (1.6M in hexane, 6.7 ml). After 30 minutes, a solution of 2-(3-methoxybenzyl)cyclooctanone (2.4 g) in THF (10 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 residue was purified by chromatography on silica gel to afford 1-(hydroxy)-1-(4,5-diphenyloxazol-2-yl)-2-(3-methoxybenzyl)cyclooctane (3.7 g). MS (m/z): 468 (M+ +1) IR (Neat): 3400 cm-1NMR (CDCl3, δ): 1.2-2.0 (12H, m), 2.2-2.8 (3H, m), 3.38 (1H, s), 3.66 (3H, s), 6.5-6.8 (3H, m), 7.07 (1H, t, J=8 Hz), 7.3-7.8 (10H, m)

Provenance & Evidence