4-Methylpyridine → 4-[2-(3-Cyclopentyloxy-4-methoxyphenyl)-2-hydroxyethyl]pyridine

Participants

Reaction Steps

From 4-methylpyridine (3.00 g, 32.1 mmol), n-butyllithium (32.1 mmol), and Intermediate 1 (6.82 g, 31.0 mmol). The crude product was subjected to chromatography [SiO2 ; EtOAc-hexane, 3:2 (500 ml) to 4:1 (1000 ml) then EtOAc-methanol, 9:1 (1500 ml)] to afford the title compound (9.68 g) as fine white needles m.p. 97-101° C. (from toluene). δH (CDCl3) 1.5-2.0 (8 H, br m, (CH2)4), 2.45(1 H, br, s, CHOH), 2.96 (2 H, d, J 6.5 Hz, CH2 pyridine), 3.80 (3 H, s, OMe), 4.70 (1 H, br, m, OCHCH2), 4.81 (1 H, t, J 6.5 Hz, CHOH), 6.76(3 H, s, ArH ortho to OMe+2×ArH meta to OMe), 7.00 (2 H, dm, J 4.5 Hz, pyridine H3, H5), and 8.33 (2 H, dm, J 4.5 Hz, pyridine H2, H6).

Provenance & Evidence