Trifluoroacetic acid → HCID 86087052, compound

Participants

Reaction Steps

A CH2Cl2 solution (15 mL) of 4-hydroxy-3-methyl-2,4-bis[3-(methyloxy)phenyl]-2-cyclobuten-1-one (246) (0.464 g, 1.50 mmol, 1 equiv) was cooled to ca. 0° C. Triethylsilane (3.02 mL, 1.0 M, 1.5 equiv) was added followed by TFA. After 5 min, the ice bath was removed and the reaction was allowed to warm to ambient temperature. After an additional 2 h, the reaction was quenched with 50% saturated aqueous NaHCO3. The organic portion was separated and pooled with those extracted using EtOAc (3×20 mL). The organic portions were dried (Na2SO4), filtered, and concentrated. Radial chromatography (SiO2, 2 mm plate, 80:20; hexanes/EtOAc) afforded the title compound as a yellow oil (0.374 g, 85%). 1H NMR (CDCl3, 300 MHz) δ 7.38-7.30 (m, 4H), 6.96-6.80 (m, 4H), 4.69 (s, 1H), 3.89 (s, 3H), 3.83 (s, 3H), 2.49 (s, 3H). TLC (80:20; hexanes/EtOAc): Rf=0.46.

Provenance & Evidence