Ethyl Acetate → HCID 69216503, compound

Participants

Reaction Conditions

Reaction Steps

A solution of {4-[8-bromomethyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl]-phenyl}-acetic acid methyl ester (Compound 47, 1.1 g, 2.4 mmol) in triethyl amine (2 mL) and N,N-dimethylformamide (10 mL) was sparged with argon and treated with trimethylsilylacetylene (2 mL, 14.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.135 g, 0.192 mmol). The resulting reaction mixture was heated at 95° C. for 20 h at the end of which it was cooled to ambient temperature and subjected to flash column chromatography over silica gel (230-400 mesh) using 1-7% ethyl acetate in hexane as the eluent to afford the title compound as an oil (0.715 g, 63%). 1H NMR (300 MHz, CDCl3): δ7.49 (d, 1H, J=2.1 Hz), 7.47 (d, 2H, J=8.2 Hz), 7.37 (d, 1H, J=2.1 Hz), 7.25 (d, 2H, J=8.2 Hz), 3.70 (s, 3H), 3.63 (s, 2H) 3.55 (s, 2H), 1.83 (s, 2H), 1.35 (s, 6H), 1.34 (s, 6H), 0.20 (s, 9H).

Provenance & Evidence