Potassium Carbonate → HCID 66707351, compound

Participants

Reaction Steps

4-(Trifluoromethoxy)benzaldehyde (125) (0.928 g, 4.88 mmol), K2CO3 (2.8 g, 20 mmol) and 18-crown-6 (0.04 g, 0.15 mmol) were added to a solution of [4-(methoxycarbonyl)benzyl]triphenylphosphonium bromide (124) (2.00 g, 4.07 mmol) in THF (60 mL) and CH2Cl2 (40 mL). The mixture was refluxed under N2 for 18 h, and then partitioned between EtOAc and water. The organic layer was washed with brine and the solvent was removed. Column chromatography of the residue on silica gel, eluting with 19:1 hexanes:EtOAc, gave a crude product which was recrystallised from hexanes to give methyl 4-{(E)-2-[4-(trifluoromethoxy)phenyl]ethenyl}benzoate (126) (0.549 g, 42%) as white flakes: mp (hexanes) 120-122° C.; NMR (CDCl3) δ 8.03 (d, J=8.4 Hz, 2H), 7.51-7.58 (m, 4H), 7.16-7.24 (m, 3H), 7.09 (d, J=16.3 Hz, 1H), 3.93 (s, 3H). APCI MS m/z 323 [M+H]+.

Provenance & Evidence