Triethyl phosphite → Diethyl (2-phenylprop-2-en-1-yl)phosphonate

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Reaction Steps

(Formula I, X=P(O), R1=phenyl, R=—OCH2CH3, n=2). α-(Bromomethyl)styrene was treated with an equimolar ratio of triethylphosphite at reflux for 1 h. After the mixture was cooled to room temperature, the by-product, ethyl bromide, was removed under reduced pressure, and the product α-(diethoxyphosphorylmethyl)styrene was obtained in quantitative yield as a yellowish syrup: 1H NMR (CDCl3) δ 1.20 (6H, t, 2×OCH2CH3, J 7.5 Hz), 3.05 (2H, d, CH2P(O), J 22.5 Hz), 4.00 (4H, m, 2×OCH2CH3), 5.35 (1H, d, olefinic proton, J 6.0 Hz), 5.50 (1K, d, olefinic proton, J 6 Hz), 7.25-7.55 (5H, m, aromatic protons).

Provenance & Evidence