Ethyl Acetate → HCID 86669890, compound

Participants

Reaction Steps

To a solution of 1-(2-(2-(1-(4-fluorophenyl)cyclohexyl)ethyl)naphtho[1,2-d]oxazol-7-yl)ethane-1,2-diol (Preparation 42D, 0.051 g, 0.117 mmol) in methanol (1 mL) at 0° C. was added a solution of sodium periodate (0.038 g, 0.176 mmol) in water (1.000 mL) dropwise and the mixture was stirred for 30 mins at the same temp. Next, about 5 mL of ethyl acetate was added and the mixture was stirred for an addition 1 hr at 0-10° C. The mixture was extracted with EtOAc, washed with brine, dried over sodium sulfate, and evaporated to give the desired 2-(2-(1-(4-fluorophenyl)cyclohexyl)ethyl)naphtho[1,2-d]oxazole-7-carbaldehyde as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 10.17 (1H, s), 8.51 (1H, d, J=8.58 Hz), 8.44 (1H, s), 8.09 (1H, dd, J=8.58, 1.32 Hz), 7.89 (1H, d, J=9.02 Hz), 7.68 (1H, d, J=9.02 Hz), 7.35 (2H, dd, J=9.02, 5.28 Hz), 7.02 (2H, t, J=8.69 Hz), 2.66-2.72 (2H, m), 2.15-2.22 (2H, m), 1.17-1.92 (10H, m).

Provenance & Evidence