Dichloromethane → (S)-1-(5-(prop-1-en-2-yl)pyridin-3-yl)ethanol

Participants

Reaction Steps

A stirred solution of (S)-1-(5-bromopyridin-3-yl)ethanol (950 mg, 4.7 mmol), potassium isopopenyltrifluoroborate (730 mg, 4.94 mmol), and Et3N (1.95 mL, 14.1 mmol) in iPrOH (30 mL) and H2O (15 mL) was degassed with argon for 10 min and then PdCl2 (dppf).CH2Cl2 (192 mg, 0.24 mmol) was added and the reaction mixture was heated to reflux for 4 h. The solution was cooled to room temperature and diluted with Ether and H2O. The layers were separated and the aqueous layer was extracted with Ether (2×50 mL). The combined organic layer was washed with brine, dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (60% EtOAc in hexanes) to provide 520 mg of (S)-1-(5-(prop-1-en-2-yl)pyridin-3-yl)ethanol.

Provenance & Evidence