4-Methyloxybenzyl chloride → HCID 67504897, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of compound 22 (3.20 g, 17.82 mmol), p-methoxybenzyl chloride (8.37 g, 53.45 mmol), K2OC3 (7.38 g, 53.45 mmol), and n-Bu4NI (1.65 g, 4.45 mmol) in anhydrous DMF (20 mL) was heated at 80° C. for 10 hours. The reaction mixture was extracted with ethyl acetate (3×100 mL), washed with water, dried over Na2SO4, filtered, and concentrated. The crude material was purified by silica gel column chromatography (Hexane/EtOAc, 3:2) to give 4.75 g (89%) of 23 as yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 3.81 (s, 3H), 5.38 (s, 2H), 6.78-6.98 (m, 2H), 7.13 (d, 1H, J=7.6 Hz), 7.34-7.60 (m, 4H), 7.80 (d, 1H, J=8.8 Hz), 8.76-8.88 (m, 1H).

Provenance & Evidence