Potassium Carbonate → HCID 59016049, compound

Participants

Reaction Steps

To a solution of 5-[3-(4-hydroxyphenyl)propyl]-4-methyl-2,4-dihydro-[1,2,4]triazol-3-one (Example 1, step C) (0.350 g, 1.50 mmol) in DMF (5 mL), was added 3-phenoxybenzyl chloride (0.94 g, 4.29 mmol) followed by potassium carbonate powder (0.74 g, 5.35 mmol). The mixture was stirred at rt under nitrogen overnight. The reaction mixture was partitioned between ethyl acetate (20 mL) and water (20 mL). The organic phase was dried over MgSO4 and filtered. Evaporation of solvent gave a crude product, which was purified on a silica gel column (125 mL SiO2) eluting with 50% EtOAc/hexanes to give the titled compound as colorless oil (0.0.78 g, 87%). 400 MHz 1H NMR (CDCl3) δ 7.32 (q, J=7.6 Hz, 4H), 7.30−7.25 (m, 3H), 7.20−6.90 (m, 10H), 6.97 (d, J=8.8 Hz, 2H), 6.87 (d, J=8.8 Hz, 2H), 5.01 (s, 2H), 4.91 (s, 2H), 3.16 (s, 3H), 2.63 (t, J=7.2 Hz, 2H), 2.46 (t, J=7.6 Hz, 2H), 1.94 (quintet, J=7.6 Hz, 2H); Mass (M+H+)=598.4.

Provenance & Evidence