Trifluoroacetic acid → HCID 131727576, compound

Participants

Reaction Steps

To a solution of (E)-methyl 3-(3-methoxy-3-oxoprop-1-enyl)-2-naphthoate (1.65 g, 6.09 mmol) in 15 mL of methylene chloride was added trifluoroacetic acid (0.07 mL, 0.91 mmol) and N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (2.34 mL, 9.13 mmol). The reaction mixture was allowed to stir at ambient temperature for 18 h. The solution was concentrated in vacuo and purified (ISCO, elution with 0-25% EtOAc/hexane) to afford 2.1 g (86%) of the title compound as an oil. 1H NMR (CDCl3): δ 8.34 (s, 1H), 8.15 (s, 1H), 7.87-7.80 (m, 2H), 7.58-7.53 (m, 1H), 7.50-7.41 (m, 3H), 7.39-7.33 (m, 2H), 7.30-7.25 (m, 1H), 4.57-4.51 (m, 1H), 3.94 (s, 3H), 3.74 (ABq, 2H), 3.68 (s, 3H), 3.36-3.31 (m, 1H), 3.27-3.20 (m, 1H), 3.07-3.02 (m, 2H), 2.80-2.75 (m, 1H). LRMS (ESI): 404.0 (M+H)+.

Provenance & Evidence