Tributylvinyltin → 2-Pyridinemethanol, 4-ethenyl-

Participants

Reaction Conditions

Reaction Steps

Bis(triphenylphosphine)palladium(II) dichloride (94 mg, 0.134 mmol) was added to a degassed solution of (4-bromo-pyridin-2-yl)-methanol (252 mg, 1.34 mmol) and tributyl(vinyl)tin (0.588 mL, 2.01 mmol) in toluene (10 mL) under nitrogen and the reaction mixture was stirred at 50° C. for 18 hours. Additional tributyl(vinyl)tin (0.176 mL, 0.67 mmol) and bis(triphenylphosphine)palladium(II) dichloride (47 mg, 0.067 mmol) were added and stirring was continued for 18 hours at 80° C. under nitrogen. The reaction mixture was cooled to room temperature and silica gel was added. The solvent was evaporated and the residue was purified by silica gel chromatography using a gradient of iso-hexanes/ethyl acetate 1:2 to 1:4 to afford the title compound (282 mg, 1.34 mmol) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ3.60-3.80 (br s, 1H), 4.78 (s, 2H), 5.52 (d, J=10.9 Hz, 1H), 6.01 (d, J=17.6 Hz, 1H), 6.69 (dd, J=17.6, 10.9 Hz, 1H), 7.22 (d, J=5.4 Hz, 1H), 7.27 (s, 1H), 8.52 (d, J=5.4 Hz, 1H).

Provenance & Evidence