Ethyl 3-methylpenta-2,4-dienoate → 3-{3-[4-(2-Methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-but-2-enoic acid ethyl ester

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Reaction Steps

Following a procedure analogous to that used in Example step 1c, but using 3-methyl-penta-2,4-dienoic acid ethyl ester and 4-(2-methyl-quinolin-4-ylmethoxy)-benzaldehyde oxime from step 1b, the crude reaction was partitioned between ethyl acetate and water, and 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 ethyl acetate:hexane (gradient) to give 3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-but-2-enoic acid ethyl ester (0.93 g, 84%) as a mixture of diasteromers. MS found: (M+H)+=431.

Provenance & Evidence