Triethylamine → HCID 19993500, compound

Participants

Reaction Steps

To a solution of diethyl 2,3-dihydroxypropoxymethylphosphonate (4.15 g, 17.lmmol), triethylamine (1.9 g, 2.62 ml, 18.81 mmol), 4-dimethylaminopyridine (84mg, 0.7 mmol) and t-butyldimethylchlorosilane (2.92 g, 19.4 mmol) in dichloromethane (50 ml) was stirred for 16 hours at 20° C. under nitrogen. The solution was washed with water (50 ml), saturated ammonium chloride (50 ml) and dried (Na2SO4). The solvents was evaporated to leave a yellow oil which was chromatographed on silica eluting with ethyl acetate affording diethyl 3-t-butyldimethylsilyloxy-2-hydroxypropoxymethylphosphonate (4.35 g, 71%) as a pale lemon liquid. νmax (film) 3400, 1460 , 1240, 1100, 1020 and 960 cm-1 ; δH (CDCl3) 0.05(6H, s, (CH3)2Si), 0.86(9H, s,(CH3)3C), 1.31(6H, t, J7.3 Hz, 2×CH2CH3), 2.50 (1H, br.s, D2O exchangeable, OH), 3.70(7H, m, CH2OSi+CHOH+CH2OCH2P), 4.12(4H, m, 2×CH2CH3); m/z 357(MH+,3%), 341 (M-CH3+,4%); Found: C,46.89; H,9.23%; C14H33O6PSi requires C,47 17; H,9.33%

Provenance & Evidence