Reaction Steps
A solution of 2 (952 mg, 1.82 mmol), benzyl 4-ethynylbenzoate (472 mg, 2.00 mmol), Pd(PPh3)2Cl2 (128 mg, 0.18 mmol), K2CO3 (250 mg, 1.81 mmol), and Et3N (238 mg, 2.36 mmol) in DMF (4 mL) was stirred for 24 hours at room temperature. Water (5 mL) was added to the mixture and then extracted with EtOAc (3×30 mL). The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. MPLC purification (Hex:EtOAc/5:1) of the residue gave 3 as a solid foam (600 mg, 52%). 1H NMR (400 MHz, CDCl3) δ 8.55 (s, 1H), 8.11-8.06 (m, 3H), 7.87 (d, J=8.0 Hz, 1H), 7.68 (d, J=8.0 Hz, 2H), 7.52 (s, 1H), 7.47-7.34 (m, 5H), 5.38 (s, 3H), 4.19 (q, J=7.2 Hz, 2H), 3.67 (s, 2H), and 1.28 (t, J=7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 183.86, 169.64, 165.88, 149.62, 142.04, 137.57, 136.41, 135.95, 135.92, 135.39, 133.02, 132.40, 131.08, 130.02, 129.93, 128.91, 128.66, 128.55, 126.69, 125.60, 124.44, 122.06, 99.57, 84.06, 67.32, 61.77, 35.25, and 14.42.
