Benzyl Bromide → [(Cyclopent-3-en-1-yloxy)methyl]benzene

Participants

Reaction Steps

To a cooled solution of cyclopent-3-enol (30.40 g, 0.36 mol) in THF (300 mL) at 0° C. was added NaH (18.82 g, 0.47 mol, 60% in mineral oil). After effervescence had ceased, benzyl bromide (80.45 g, 0.47 mol) was added dropwise at 0° C. over a 45 min period. The reaction mixture was allowed to warm to RT over a 6 h period. Excess NaH was quenched with MeOH (120 mL) at a temperature below 5° C. The mixture was warmed to RT, diluted with H2O, and the two layers were separated. The aqueous layer was extracted with EtOAc. The organic layers were combined, concentrated, and purified by column chromatography eluting with petroleum ether and EtOAc (PE/EA=40/1 to 30/1) to give the title compound as an oil (45.28 g, 72%). 1H NMR (400 MHz, CDCl3) δ ppm 2.38-2.41 (m, 2 H), 2.49-2.54 (m, 2 H), 4.20-4.24 (m, 1 H), 4.42 (s, 2 H), 5.62 (s, 2 H), 7.17-7.28 (m, 5 H).

Provenance & Evidence