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

Beteiligte Stoffe

Reaktionsschritte

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 subject 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 (SH, br m, (CH2)4, 2.45(1H, br, s, CHOH), 2.96 (2H, d, J 6.5 Hz, CH2 pyridine), 3.80 (3H, s, OMe), 4.70 (1H, br, m, OCHCH2), 4.81 (1H, t, J 6.5 Hz, CHOH), 6.76 (3H, s, ArH ortho to OMe+2×ArH meta to OMe), 7.00 (2H, dm, J 4.5 Hz, pyridine H3, H5), and 8.33 (2H, dm, J 4.5 Hz, pyridine H2, H6).

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