Triethyl phosphite → Diethyl 12-(1,3-dioxoisoindolin-2-yl)dodecylphosphonate

Participants

Reaction Conditions

Reaction Steps

2-(12-bromododecyl)isoindoline-1,3-dione (9.30 g, 23.6 mmol) was combined with triethylphosphite (11.76 g, 70.7 mmol) in a round bottom flask and the mixture heated and stirred at 135° C. for 16 hours. The reaction mixture was then put under hi-vacuum at 90° C. for 4 hours. The product was then obtained as a clear oil after column chromatography in ethyl acetate. (8.96 g, 84% yield). 1H NMR (400.14 MHz, CDCl3) δ 7.80 (dd, J=5.43, 3.04 Hz, 2H), 7.67 (dd, J=5.47, 3.05 Hz, 2H), 4.08-4.02 (m, 4H), 3.63 (t, J=7.33 Hz, 2H), 1.73-1.45 (m, 6H), 1.32-1.11 (m, 22H). 13C{1H} NMR (100.62 MHz, CDCl3) δ 168.4 (2C), 133.7 (2C), 132.1 (2C), 123.0 (2C), 61.30 (d, J=6.5 Hz, 2C), 37.96, 30.51, (d, J=17.0 Hz), 29.41 (2C), 29.35, 29.25, 29.07, 28.98, 28.49, 26.75, 25.55 (d, J=140.1 Hz), 22.29 (d, J=5.0 Hz), 16.39 (d, J=6.1 Hz, 2C). 31P{1H} NMR (161.97 MHz, CDCl3): δ 33.38. MS (ESI, m/z): 452.235 (M+, 100%). Exact mass calculated (found) for [M+H]+, m/z): 452.256039 (452.254800). Analysis calculated (found) %: C, 63.84 (63.41), H, 8.48 (8.53).

Provenance & Evidence