Tetrahydrofuran → HCID 86680608, compound

Participants

Reaction Steps

To a solution of 5-(3-methoxyphenyl)picolinaldehyde (0.75 g, 3.5 mmol), in THF (7 mL) was added methyl magnesium bromide (0.17 g, 8.8 mmol) under nitrogen at −40° C./ The reaction was brought to rt and then stirred at rt for 2 h. The contents were diluted with ethyl acetate (150 mL), quenched with ammonium chloride solution (100 mL), the organic layer washed with brine solution (2×100 mL), the layers separated, the organic layer was dried over sodium sulphate and distilled off to get the crude product. The compound was purified by flash chromatography (100-200 microns; 15% ethyl acetate in hexane) to give 1-(5-(3-methoxyphenyl)pyridin-2-yl)propan-1-ol (450 mg, 53% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.73 (s, 1H), 8.04 (d, 1H), 7.52 (d, 1H), 7.38 (t, 1H), 7.26 (s, 1H), 7.23 (d, 1H), 6.95 (d, 1H), 5.28 (d, 1H), 4.54 (q, 1H), 3.81 (s, 3H), 1.7 (m, 1H), 1.8 (m, 1H), 0.86 (t, 3H); LC-MS m/z calcd for [M+H]+ 244.13. found 244.0.

Provenance & Evidence