Sodium hydride → HCID 86647344, compound

Participants

Reaction Steps

To a stirred suspension of NaH (258 mg of a 55% dispersion in mineral oil) in THF (9 mL) at 0° C. under argon, was added a solution of (3-butyl-5-methyl-isoxazol-4-yl)-methanol (1.0 g, 5.9 mmol) in THF (18 mL) dropwise. The reaction mixture was warmed to room temperature. After 30 min the reaction mixture was cooled to 0° C. and a solution of 3,6-dichloropyridazine (908 mg, 6.1 mmol) in THF (18 mL) was added dropwise. After 16 h the reaction mixture was warmed to room temperature then quenched with water and extracted with ethyl acetate. The combined organic phases were dried, filtered and concentrated then purified by chromatography (silica, 10 to 60% ethyl acetate in heptane) to give the title compounds (1.31 g, 66%) as a light yellow liquid.

Provenance & Evidence