Pyridine → HCID 86607685, compound

Participants

Reaction Steps

A solution of cyclobutanol (1.00 g, 13.9 mmol) in 25 ml of DCM was chilled to −20° C. and dry pyridine (1.35 ml, 16.6 mmol) added, followed by trifluoromethanesulfonic anhydride (2.33 ml, 13.9 mmol) (in 5 ml of DCM). The solution was allowed to warm to room temperature over 1 hr. Pentane (40 mL) was added and the resulting mixture shaken and filtered. The filtrate was concentrated under reduced pressure with a room temperature bath until all volatile solvents were removed. The residual oil was chilled to −20° C. and diphenylsulfane (10.2 ml, 61.0 mmol) added. The mixture was stirred at 25° C. for 20 hr, warmed to 45° C. for 30 minutes and cooled to room temperature. Pentane was added, the solution shaken and the resulting solid collected by vacuum filtration to give cyclobutyldiphenylsulfonium trifluoromethanesulfonate (1.82 g, 4.86 mmol, 35.0%). MS: m/z (ES+): 241 [C16H17S]+. 1H NMR (D6-DMSO): δ 8.10 (dt, 4H, J1=7.8, J2=3.1), 7.84-7.72 (m, 6H), 5.90-5.78 (m, 1H), 5.15 (ddd, 2H, J1=14.9, J2=10.3, J3=1.4), 4.48 (t, 2H, J=14.2), 2.45 (dd, 2H, J1=13.8, J2=7.1).

Provenance & Evidence