Triethylamine → Methyl 4-trimethylsilylethynylbenzoate

Participants

Reaction Conditions

Reaction Steps

A stirred solution at room temperature of methyl 4-bromobenzoate (8.84 g, 41.11 mmol), Pd(PPh3)2Cl2 (840 mg, 1.20 mmol) and Cul (455 mg, 2.39 mmol) in anhydrous THF (200 ml) was saturated with nitrogen for 15 min. Then, the solution under nitrogen was cooled down at 0° C., and trimethylsilylacetylene (7.2 ml, 50.91 mmol) and triethylamine (22 ml, 157.8 mmol) were added successively. The reaction mixture was allowed to warm up at room temperature. After 2 h, Pd(PPh3)2Cl2 (100 mg) and Cul (80 mg) and trimethylsilylacetylene (0.5 ml) were added again, and the reaction mixture was stirred overnight. Then, the reaction mixture was diluted with AcOEt and successively washed with a saturated aqueous solution of NH4Cl and brine, dried over MgSO4, filtered and concentrated. The crude residue was then purified by flash chromatography on silica gel (AcOEt/hexane:5/95□10/90) to afford the title compound XXXI (9.05 g, 38.95 mmol, 94% yield) as a yellow sticky solid. 1H NMR: (400 MHz, CDCl3) δ (ppm): AB system (δA=7.67, δB=7.22, JAB=8.5 Hz, 4H), 3.63 (s, 3H), 0.00 (s, 9H).

Provenance & Evidence