Pyridine → 1-[N-acetyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene

Participants

Reaction Steps

To a solution of 1-(4,5-diphenyloxazol-2-yl)methylamino-2,3-dihydro-4-methoxy-1H-indene (0.22 g) and pyridine (0.2 ml) in dichloromethane (5 ml) was added acetyl chloride (0.15 ml) at 0° C. The mixture was stirred for 1.5 hours at the same temperature and partitioned between ethyl acetate and 1N hydrochloric acid. The organic layer was washed with water, sat. NaHCO3, and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to give 1-[N-acetyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene (0.08 g). MS (m/z): 439 (M+ +1) IR (Nujol): 1640 cm-1NMR (CDCl3, δ): 7.65-7.45 (4H, m), 7.40-7.20 (6H, m), 7.19-7.02 (1H, m), 6.82-6.60 (2H, m), 6.40 (0.5H, t, J=7.5 Hz), 5.56 (0.5H, t, J=7.5 Hz), 4.72 (0.5H, d, J=8.1 Hz), 4.42 (1H, m), 4.19 (0.5H, d, J=8.1 Hz), 3.81 (1.5H, s), 3.78 (1.5H, s), 2.37 (1.5H, s), 3.15-2.92 (1H, n), 2.90-2.64 (1H, m), 2.62-2.42 (1H, m), 2.40-2.10 (1H, m), 2.37 (1.5H, s), 2.35 (1.5H, s)

Provenance & Evidence