Methanol → HCID 19801610, compound

Participants

Reaction Steps

A solution of diethyl [[3-(2-aminoethyl)phenyl]methyl]phosphonate (Example D) (3.6 g, 13.2 mmol) in toluene (15 ml) and triethylamine (2.7 g, 26.4 mmol) is cooled in an ice/salt bath and a solution of ethyl bromoacetate (2.2 g, 13.2 mmol) in toluene (8 ml) is added dropwise over 20 minutes. A gum forms and methanol (5 ml) is added and stirred an additional two hours. After evaporation of the solvent, the residue is dissolved in ethyl acetate (75 ml) and washed with water (20 ml, and 10 ml) and then saturated sodium chloride solution (10 ml). The organic layer is dried over magnesium sulfate, filtered, and evaporated to give an oil (4.3 g). Chromatography over silica gel gives an analytical, colorless oil. 1H-NMR: 4H, m, 7.33-7.0 ppm; 6H, m, 4.33-3.86; 2H, s, 3.40; 2H, d, 3.13; 4H, m, 2.90-2.70; 1H, s, 1.8; 9H, m, 1.33-1.10.

Provenance & Evidence