Triethylamine → HCID 46175563, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3 (18.1 g, 45.9 mmol), Et3N (12.8 mL, 91.9 mmol), Pd(PPh)2Cl2 (1.6 g, 5% mol), CuI (0.7 g, 8% mol), and TMS-acetylene (19.6 mL, 137.8 mmol) in degassed THF (180 mL) is heated at 60° C. overnight. The mixture is cooled to rt, and then partitioned between H2O and EtOAc. This mixture is filtered through Celite to remove the insoluble material. The two layers of the filtrate are separated, and the organic layer is washed H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude material is purified on silica gel with heptane/EtOAc as eluant to give 15.6 g (93%) of the product 4 as beige solid. 1H NMR (CDCl3) δ 7.15-7.00 (m, 2H), 6.41 (br s, 1H), 4.26 (q, J=7.1 Hz, 2H), 1.31 (t, J=7.1 Hz, 3H), 0.27 (s, 9H); 19F NMR (CDCl3) δ −57.59 (s, 3F), −118.15 (s, 1F); MS 364 (M+1, 100%).

Provenance & Evidence