Pyridine → HCID 86757351, compound

Participants

Reaction Steps

To a solution of 82 (0.2 g, 0.9 mmol) in 2 mL of anhydrous CH2Cl2 at 0° C. was added anhydrous pyridine (71 mg, 0.9 mmol) and methylsulfonyl chloride (0.1 g, 0.9 mmol) under argon (FIG. 2N). The solution was stirred at room temperature for 6 h. The reaction was carefully quenched with water and extracted with CH2Cl2 (3×10 mL). The combined organic extracts were washed with water, dried (MgSO4), and concentrated in vacuo. Chromatography on silica gel (EtOAc:hexanes, 5:95) gave the desired methylsulfonyloxy derivative 124 as a colorless oil (0.22 g, 84%). 1H NMR (CDCl3) δ7.51-7.53 (dd, 1 H, J=7.6 Hz and 2.6 Hz, ArH), 7.40-7.42 (dd, 1 H, J=7.9 Hz and 2.8 Hz, ArH), 7.26-7.30 (m, 2 H, ArH), 3.66 (t, 2 H, J=1.3 Hz CH2), 3.24 (s, 3 H, CH3), 2.11-2.13 (m, 2 H, CH2), 1.26-1.41 (m, 4 H, CH2), 0.84-0.87 (t, 3 H, J=7.1 Hz, CH3); 13C NMR (CDCl3) δ147.63, 130.77, 129.18, 127.82, 127.59, 123.20, 84.74, 74.54, 38.50, 30.52, 21.97, 21.77, 18.37, 13.53.

Provenance & Evidence