Triethylamine → HCID 86712692, compound

Participants

Reaction Conditions

Reaction Steps

A solution of triethylsilyl acetylene (0.27 mL, 1.5 mmol) in degassed DMF (4 mL) and Et3N (2.0 mL, 15 mmol) was added to a mixture of methyl 2-(2-bromo-4-methylphenyl)acetate (A84) (0.30 g, 1.2 mmol), PdCl2(PPh3)2 (0.043 g, 0.062 mmol), CuI (0.012 g, 0.062 mmol) and t-Bu3PH.BF4 (0.018 g, 0.062 mmol) in degassed DMF (10 mL). The resulting mixture was heated at 70° C. for 17 hours then diluted with EtOAc and passed through a plug of Celite, washing with EtOAc (150 mL). The filtrate was concentrated under reduced pressure and adsorbed onto silica gel and purified by column chromatography (Biotage Isolera, 40 g SiO2 cartridge, 0-15% EtOAc in petroleum spirits) to yield the title compound A85 as a yellow oil (0.326 g, 72% purity contaminated with starting material); 1H NMR (400 MHz, CDCl3) δ 7.32 (s, 1H), 7.15 (d, J=7.8 Hz, 1H), 7.12-7.08 (m, 1H), 3.82 (s, 2H), 3.68 (s, 3H), 2.31 (s, 3H), 1.05 (t, J=7.9 Hz, 9H), 0.72-0.64 (m, 6H).

Provenance & Evidence