Diethyl Ether → HCID 21219682, compound

Participants

Reaction Conditions

Reaction Steps

Diethyl cyanophosphonate (0.50 g, 3.06 mmol) and trimethylsulfoxonium iodide (0.673 g, 3.06 mmol) were added to dimethylacetamide (1 mL) which was heated to 80° C. for 1 hour. Then ether (9 mL) containing 1 mL of acetone was added to give 0.47 g (78% yield) of a viscous residue which was crystallized within 15 hours. It was washed by CH2Cl2 and dried under vacuum, and analyzed by NMR and mass spectrometry. 31P NMR (D2O) δ (ppm) -19.7 (t, 3JPH =9.15 Hz); 1H NMR (D2O) δ (ppm) 1.22 (t), 3.78 (s), and 4.05 (qnt); 13C NMR (D2O) δ (ppm) 118.1 (d, 1JCP =178.9 Hz), 63.3 (d, 1JCP =6.3 Hz), 39.5, 15.0 (d, 3JCP =6.87 Hz). Mass spectral analysis (FAB+, DTT:DTE, 1:1) detected a peak at m/z 320.1, corresponding to the complex [[+OS(CH3)3 -O(OC2H5)POCN] [OS(CH3)3 ]+ ], the presence of a cation at m/z 93 ([OS(CH3)3 ]+) and an anionic species (FAB-, DTT:DTE, 1:1) at m/z 134 [NCP(O)(OC2H5)O - ].

Provenance & Evidence