Reaction Steps
To a solution of 5 (209 mg, 0.31 mmol) in 3 mL CH2Cl2 was added 1-fluoropyridinium triflate (81 mg, 0.33 mmol), and then the mixture stirred at room temperature until no 5 was detected by NMR. The resulting mixture was diluted with 40 mL Et2O, washed with brine (2×10 mL), dried over MgSO4, filtered, and then concentrated in vacuo. MPLC purification (Hex/EtOAc 9:1) gave 6 (40 mg, 19%) as a yellow amorphous solid. 1H NMR (400 MHz, CDCl3) δ 7.94 (s, 1H), 7.77-7.63 (m, 6H), 7.57 (s, 1H), 7.48-7.40 (m, 5H), 4.25 (t, J=7.2 Hz, 2H), 4.16 (q, J=7.2 Hz, 2H), 3.72 (s, 2H), 3.48 (t, J=6.8 Hz, 2H), 1.65-1.61 (m, 2H), 1.50-1.44 (m, 2H), and 1.26 (t, J=7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 187.16, 169.94, 168.50, 143.96, 143.10, 140.65, 135.88, 135.17, 134.22, 134.17, 132.37, 132.31, 132.11, 131.68, 129.96, 129.51, 129.17, 129.13, 128.96, 128.45, 127.58, 127.38, 123.46, 121.80, 121.19, 120.18, 120.03, 116.97, 112.58, 61.52, 43.64, 37.21, 35.33, 27.32, 25.76, and 14.44; 19F NMR (376 MHZ, CDCl3) δ −174.33.
