(3-Bromopropyl)benzene → Ethyl-4-benzyloxy-2-methyl-6-(3-phenyl-propoxy)-benzoate

Participants

Reaction Conditions

Reaction Steps

Ethyl-4-benzyloxy-2-hydroxy-6-methyl-benzoate (0.5 g, 1.8 mmol) is dissolved in DMF (10 mL) and 60% sodium hydride (0.07 g, 1.8 mmol) is added and stirred 20 minutes, forming a clear solution. Then 1-bromo-3-phenyl propane (0.27 mL, 1.8 mol) is added and this mixture is heated at 100° C. for 4 hours and stirred at room temperature overnight. The solvent is removed in vacuo and the residue purified by flash chromatography (silica, 5% ethyl acetate in hexanes) to give the title compound: 1H NMR (300 MHz, CDCl3) δ 7.17-7.40 (m, 10H), 6.39 (d, 1H), 6.33 (d, 1H), 5.03 (s, 2H), 4.38 (q, 2H), 3.91 (t, 2H), 2.77 (t, 2H), 2.30 (s, 3H), 2.05 (m, 2H), 1.38 (t, 3H); MS (EI) 404 (M)+.

Provenance & Evidence