Acetone cardice → 3-[4-(6-Methoxy-3-methyl-2-thiophen-3-yl-naphthalen-1-yloxy)-phenyl]-acrylic acid ethyl ester

Participants

Reaction Steps

To a solution of triethylphosphonoacetate (0.242 mL, 1.22 mmol) in dry THF (4 mL) at −78° C. was slowly added 1.6 M nBuLi (0.812 mL, 1.30 mmol) then stirred for 30 min at above temperature. 4-(6-Methoxy-3-methyl-2-thiophen-3-yl-naphthalen-1-yloxy)-benzaldehyde (200) (0.304 g, 0.812 mmol) in dry THF (4 mL) was added to the reaction mixture slowly then stirred reaction mixture at above temperature for 1 h. The reaction was taken out of the acetone-dry ice bath and stirred at room temperature for 3 h. The reaction was quenched with 1 N HCl and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. The crude material was purified with a gradient of 5% EtOAc in hexanes over 60 min to afford 0.27 g (75%) of compound (201) as a yellow solid. 1H NMR (400 MHz, d-CDCl3): δ 1.28-1.32 (t, J=7.1, 7.2 Hz, 3H), 2.31 (s, 3H), 3.92 (s, 3H), 4.20-4.25 (m, 2H), 6.23 (d, J=15.9 Hz, 1H), 6.62 (d, J=8.8 Hz, 2H), 6.90-6.91 (m, 1H), 7.01-7.02 (m, 2H), 7.04-7.05 (m, 1H), 7.11-7.12 (m, 1H), 7.20-7.22 (m, 1H), 7.28 (d, J=8.8 Hz, 1H), 7.53-7.57 (m, 2H), 7.72 (d, J=9.2 Hz, 1H).

Provenance & Evidence