Sodium hydride → 4-Chloro-2-(1-cyclopropyl-2-methoxyvinyl)-3-methylpyridine

Participants

Reaction Conditions

Reaction Steps

A solution of methoxymethyl triphenylphosphonium chloride (17.9 g, 52.3 mmol) in dry THF (80 mL) was treated with NaH (2.79 g, 69.8 mmol) at 0° C. for 3 h. To this mixture was added a solution of (3-methyl-4-chloro-pyridin-2-yl)-cyclopropyl-methanone (6.82 g, 34.9 mmol) in dry THF (20 mL). The reaction mixture was heated at 40° C. overnight. The reaction mixture was cooled down to room temperature and filtered. The filtrate was concentrated to dryness. The residue was purified by flash silica column chromatography (hexane:ethyl acetate, 3:1) to afford the title compound (6.41 g, 82%). ESI-MS m/z: 224 (M+H)+; 1H NMR (CDCl3, 300 MHz) δ ppm: 8.31 (d, J=5.4 Hz, 0.5; H), 8.23 (d, J=5.4 Hz, 0.5; H), 7.17 (d, J=5.4 Hz, 1H), 6.13-6.16 (m, 1H), 3.70 (s, 1.5; H), 3.56 (s, 1.5; H), 2.38 (s, 1.5; H), 2.31 (s, 1.5; H), 1.91-1.94 (m, 0.5; H), 1.63-1.65 (m, 0.5; H), 0.66-0.72 (m, 1H), 0.56-0.62 (m, 1H), 0.35-0.38 (m, 1H), 0.26-0.33 (m, 1H).

Provenance & Evidence