3-Pentanol → CP-316311

Participants

Reaction Steps

To a solution of 3-pentanol (56 mL, 0.5205 mol) in dimethyl sulfoxide (DMSO, 760 mL) was added, portionwise, sodium hydride (60% oil dispersion, 7.64 g, 0.191 mol). After stirring at room temperature for thirty minutes, a solution of 4-chloro-2,5-dimethyl-6-(2,4,6-trimethylphenoxy)-pyridine (prepared as described in Preparation D, 47.80 g, 0.1735 mol) in tetrahydrofuran (THF, 50 mL) was added and the resulting mixture was heated at 130° C. for three hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give 68.21 g of a yellow solid. The solid was purified through silica gel column chromatography using 10% chloroform in hexane to chloroform as eluent to give 52.2064 g (92%) of the title compound of Example 2 as white crystals. mp 72.5° C. to 74° C. 1HNMR (CDCl3) δ 6.84 (s, 2H), 6.26 (s,1 H), 4.16 (m, 1H), 2.27 (s, 3H), 2.17 (s, 6H), 2.04 (s, 6H), 1.69 (m, 4H), 0.95 (t, 6H) ppm.

Provenance & Evidence