Methyl 4-(trifluoromethyl)benzoylacetate → Methyl 2-ethyl-4-oxo-6-[4-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3-carboxylate

Participants

Reaction Steps

1.00 g (3.84 mmol) of methyl 3-oxo-3-[4-(trifluoromethyl)phenyl]propanoate and 546 mg (4.23 mmol) of methyl 3-aminopent-2-enoate [Pena et al., J. Am. Chem. Soc. 124., 14552-14553 (2002)] were taken up in 4 ml of xylene, 1.50 g molecular sieve (4 Å) which had been dried by heating were added and the mixture was reacted at reflux temperature overnight. The molecular sieve was removed by filtration and washed with methanol/chloroform (1/1). The combined organic phases were concentrated on a rotary evaporator and the crude product was purified by preparative HPLC (mobile phase: acetonitrile/water, gradient 10:90→90:10). This gave 270 mg (21% of theory) of the target compound.

Provenance & Evidence