1-Bromo-3-methylbutane → 4-(benzyloxy)-1-isopentyl-2(1H)-pyridinone

Participants

Reaction Conditions

Reaction Steps

A solution of 4-benzyloxy-1H-pyridin-2-one (1.0 g, 4.97 mmol) and 1-bromo-3-methyl butane (0.715 mL, 5.96 mmol) in N,N-dimethylformamide (20 mL) was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (1.86 mL, 12.43 mmol) at 65° C. for 5 days. The mixture was cooled to 25° C. and partitioned between water and dichloromethane. The organic layer was concentrated under reduced pressure. The residue was chromatographed on silica gel, eluting with 1% methanol in dichloromethane to give the title compound (0.57 g, 42%). MS (DCI/NH3) m/z 272 (M+H)+. 1H NMR (300 MHz, CDCl3) δ 0.96 (d, J=6.25 Hz, 6 H) 1.61 (m, 3 H) 3.89 (m, 2 H) 4.99 (s, 2 H) 5.98 (dd, J=7.54, 2.76 Hz, 1 H) 6.06 (d, J=1.84 Hz, 1 H) 7.14 (d, J=7.72 Hz, 1 H) 7.39 (m, 5 H).

Provenance & Evidence