Water → HCID 66643579, compound

Participants

Reaction Steps

To a stirred suspension of sodium hydride (2.78 g of a 60% dispersion in mineral oil, 64 mmol) in THF (40 mL) at 0° C. and under argon was added solution of (5-methyl-3-propyl-isoxazol-4-yl)-methanol (7.60 g, 49 mmol) in tetrahydrofuran (40 mL) dropwise. The mixture was warmed to ambient temperature, stirred for 30 min, then cooled to 0° C. and a solution of methyl 6-chloronicotinate (8.40 g, 49 mmol) in THF (40 mL) was added dropwise. The reaction mixture was warmed to room temperature. After 2 h, water was added then the resulting mixture extracted with ethyl acetate. The combined organic extracts were dried, filtered and concentrated. Purification by chromatography (silica, 0 to 20% ethyl acetate in heptane) gave the title compound (8.4 g, 50%) as a light yellow oil. MS: m/e=413.2 [M+H]+.

Provenance & Evidence