Tributylphosphine → (2-(4-Acetamidophenoxy)-2-oxoethyl)tributylphosphonium chloride

Participants

Reaction Steps

4-Acetamidophenyl 2-chloroacetate [2] (1.138 g, 5 mmol) and tributylphosphine (0.475 g, 6 mmol) were suspended in 50 ml of anhydrous ethyl acetate and refluxed for 48 hrs. After cooling to room temperature the white precipitate was filtered, washed with ethylacetate and diethylether and dried under reduced pressure to give [6]. The crude product was crystallized twice from acetonitrile to give pure [6] in 65% yield. Identity and purity was confirmed via 1H and 13C NMR. The desired compound is isolated as colourless needles. 1H-NMR (300 MHz, d6-DMSO) δ(ppm)=10.49 (s, 1H), 7.71 (d, J=8.95 Hz, 2H), 7.12 (d, J=8.95 Hz, 2H), 4.18 (d, J=14.33, 2H), 2.41 (m, 3H), 2.06 (s, 3H), 1.55 (m, 6H), 1.41 (m, 6H), 0.91 (t, J=7.17). 31P-NMR (121.5 MHz, d6-DMSO) δ(ppm)=34.8. 13C-NMR (75 MHz, d6-DMSO) δ(ppm)=168.4, 164.7, 144.8, 137.8, 121.4, 119.9, 25.8 (d, J=47.9 Hz), 23.9, 23.3 (d, J=16.77 Hz), 22.6 (d, J=4.43 Hz), 18.2 (d, J=47.7 Hz), 13.2. mp 199° C. (dec), T5%onset 197° C.

Provenance & Evidence