Sodium hydride → methyl 3-[5-(2-tert-butylsilyloxypropan-2-yl)-3-[4-[(2-methylquinolin-4-yl)methoxy]phenyl]-4H-1,2-oxazol-5-yl]prop-2-enoate

Participants

Reaction Steps

Trimethyl phosphonoacetate (0.4 g, 2.2 mmol) was added to a suspension of sodium hydride (hexane washed) (0.088 g, 60% in oil, 2.2 mmol) in DMF (7 mL) under a nitrogen atmosphere at 0° C. The reaction was stirred for 0.5 h and the aldehyde from step 24c was added. The reaction was stirred for 1 h and then 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 (60:50) to give 3-{5-(tert-butyl-dimethyl-silanyloxymethyl)-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acrylic acid methyl ester (0.24 g, 20%) as an oil. MS found: (M+H)+=547.

Provenance & Evidence