Acetonitrile → Diethyl P-2-naphthalenylphosphonate

Participants

Reaction Steps

1-(trimethylsilyl)naphthalen-2-yl trifluoromethanesulfonate (25 mg, 0.073 mmol), Cesium Fluoride (60 mg, 0.395 mmol), Triethtyl phosphite (47 mg, 0.287 mmol), Acetonitrile (1 ml): Reaction Time 24 h; Rf: 0.3 (1:3 EtOAc:Pet. Ether); Thick oil; 15.5 mg, 82%; 1H NMR (400 MHz, CDCl3, TMS) δ 8.44 (d, J=15.6 Hz, 1H), 7.97-7.85 (m, 3H), 7.81-7.72 (m, 1H), 7.64-7.52 (m, 2H), 4.26-4.05 (m, 4H), 1.34 (t, J=7.0 Hz, 6H); 13C NMR (100 MHz, CDCl3, TMS) δ 135.0 (d, J=2.3 Hz), 134.0 (d, J=10.0 Hz), 132.3 (d, J=16.2 Hz), 128.9, 128.3 (d, J=14.7 Hz), 128.2, 127.8, 126.8, 126.4 (d, J=9.2 Hz), 125.3 (d, J=188.1 Hz), 62.1 (d, J=5.4 Hz), 16.3 (d, J=6.2 Hz); 31P NMR (162 MHz, CDCl3) δ 19.1; Mass (M+Na)+ 287; Known compound, Lit. M. Kalek, A. Ziadi, J. Stawinski, Org. Lett. 2008, 10, 4637.

Provenance & Evidence