Acetyl chloride → 4-Acetoxy-2-(3-cyclopentyloxy-4-methoxybenzyl)-benzoxazole

Participants

Reaction Steps

A solution of 2-(3-cyclopentyloxy-4-methoxybenzyl)-4-hydroxybenzoxazole (200 mg) and acetyl chloride (84 μl) in pyridine (6 ml) was stirred at room temperature, under nitrogen, for 3 hours. The reaction mixture was diluted with methanol (20 ml) and evaporated in-vacuo to yield a yellow solid. The solid was purified by flash chromatography (SiO2 ; dichloromethane; methanol (50:1)) and crystallized from ether/petroleum ether to yield the title compound (119 mg, 53%) as a white crystalline solid (mp 65-°67° C.). δH (250MHZ;d6DMSO) 1.45-1.92 (8H,m,4×CH2), 2.35 (3H,s,MeC(O)), 3.70 (3H,s,OMe), 4.24 (2H,s,CH2), 4.73 (1H,m,CH), 6.82 (1H,dd,ArH), 6.89 (1H,d,ArH), 6.95 (1H,d,ArH), 7.12 (1H,dd,ArH), 7.36 (1H,t,ArH), 7.58 (1H,dd,ArH).

Provenance & Evidence