Triphenylphosphine → HCID 86702154, compound

Participants

Reaction Steps

A solution of 1,1-(azodicarbonyl) dipiperidine (1.874 g, 7.4 mmol) in anhydrous tetrahydrofuran (10 mL) was added dropwise to a 0° C. solution of 1,3-propanesultam (0.6 g, 4.95 mmol), triphenylphosphine (1.95 g, 7.4 mmol), and 2,4-dimethoxybenzyl alcohol (1.0 g, 6.2 mmol) in anhydrous tetrahydrofuran (20 mL). The resultant solution was stirred at 0° C. for 3 hrs, warmed to room temperature and stirred for a further 16 hrs. The solution was concentrated under reduced pressure and suspended in ethyl acetate/hexanes to precipitate a white solid. The solid was removed by filtration and the filtrate purified by silica gel chromatography (25-70% ethyl acetate/hexanes) to give a pale yellow oil (0.505 g). 1H NMR (CDCl3, 300 MHz) δ 7.31-7.28 (dd, 1H, J=0.6, 7.8 Hz), 6.49-6.44 (m, 2H), 4.17 (s, 2H), 3.81 (s, 3H), 3.80 (s, 3H), 3.19-3.13 (m, 4H), 2.32-2.23 (m, 2H).

Provenance & Evidence