Sodium hydride → 3-{3-[4-(2-Methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acrylic acid tert-butyl ester

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Reaction Steps

t-Butyl dimethylphosphonoacetate (0.31 g, 1.38 mmol) was added to a suspension of sodium hydride (washed with hexanes) (0.061 g @60%, 1.5 mmol) in DMF (3 mL) cooled in an ice bath, under a nitrogen atmosphere. The reaction was stirred for 0.5 h and the product from step 10b (0.31 g, 1.38 mmol) in DMF (3 mL) was added. The reaction was stirred for 2 h at 0° C. and was complete. This was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give an oil. The product was purified by FCC on silica gel eluting methylene chloride:ethyl acetate (70:30) to give 3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acrylic acid tert-butyl ester (0.38 g, 61%) as an oil. MS found: (M+H)+=445.

Provenance & Evidence