Hydrochloric Acid → HCID 86087051, compound

Participants

Reaction Steps

A THF solution (12 mL) of 2-methyl-4,4-bis(methyloxy)-3-[3-(methyloxy)phenyl]-2-cyclobuten-1-one (245) (0.500 g, 2.02 mmol, 1 equiv) was cooled to ca. −78° C. 3-Methoxyphenylmagnesium bromide (3.02 mL, 1.0 M, 1.5 equiv) was added. After 5 min, aqueous HCl (3 N, 20 mL) was added. Extraction with EtOAc (3×20 mL) was followed by washing with 50% aqueous NaHCO3, drying (Na2SO4), filtration, and concentration to a bright yellow oil. Radial chromatography (SiO2, 4 mm plate, 80:20; hexanes/EtOAc) afforded the title compound (246) as a bright yellow oil (0.515 g, 82%). 1H NMR (CDCl3, 300 MHz) δ 7.39-7.29 (m, 4H), 7.10-6.88 (m, 4H), 3.88 (s, 3H), 3.85 (s, 3H), 2.47 (s, 3H); TLC (60:40; hexanes/EtOAc): Rf=0.23.

Provenance & Evidence