Diethyl Ether → HCID 69679626, compound

Participants

Reaction Steps

To a solution of 5-bromopicolinaldehyde (2.0 g, 10.8 mmol) in THF (20 mL) was added 3.0 M solution of ethyl magnesium bromide in diethyl ether (7.1 ml, 21.5 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred for 6 h. The reaction mixture was quenched with saturated ammonium chloride solution (20 mL) and water (15 mL), extracted with ethyl acetate (200 mL), dried over sodium sulphate and concentrated under reduced pressure to obtain crude product. The crude product was purified by a Biotage Isolera® One column (using 10% ethyl acetate and hexane (0.72 g, (45% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.57 (d, 1H), 8.01-7.98 (dd, 1H), 7.445 (d, 1H), 5.36 (d, 1H), 4.49-4.45 (dd, 1H), 1.65-1.61 (m, 2H), 0.815 (t, 3H).

Provenance & Evidence