Benzyl Bromide → HCID 67057591, compound

Participants

Reaction Steps

With reference to FIG. 7, 4-(2-(benzhydryloxy)ethyl)pyridine 3 (4.0 g, 13.82 mmol) and benzyl bromide (2.86 g, 16.73 mmol) were dissolved in 20 ml of dry acetonitrile and refluxed for 6 hrs. The solvent was removed in vacuo. After drying the residue for 2 hrs under high vacuum, it was dissolved in 30 ml of dry methanol and cooled in an ice-bath. Sodium borohydride (0.76 g, 20.05 mmol) was then added very slowly portionwise over a period of 1.5 hrs, and the solution was gradually brought to room temperature. The reaction was quenched with water after stirring for 4 h, and methanol was removed in vacuo. The residual product was dissolved in ethyl acetate, washed with water, dried (Na2SO4), and concentrated. The crude product was purified by column chromatography over silica gel (hexane:ethyl acetate 5:1) to produce 4 (5.0 g, 94%) as a colorless oil. 1H-NMR (CDCl3; 400 MHz): 2.086 (brs, 2H, H-3), 2.32-2.35 (t, 2H, J=6.8 Hz, OCH2CH2), 2.52-2.54 (t, 2H, J=5.6 Hz, H-2), 2.94-2.94 (brm, 2H, H-6) 3.52-3.55 (m, 4H, NCH2Ph, OCH2CH2), 5.34 (s, 1H, PhCH(O)Ph), 5.41-5.42 (brs, 1H, CH═C), 7.12-7.37 (m, 15H, ArH).

Provenance & Evidence