p-Toluenesulfonyl azide → (1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Participants

Reaction Steps

(2-oxo-propyl)-phosphonic acid dimethyl ester (20 g, 0.12 mol) was dissolved in toluene (500 mL) at 0° C. and NaH (4.8 g, 0.12 mol) was added in portions. After the gas evolution had ceased, a solution of 4-methyl-benzenesulfonyl azide (21.4 g, 1.1 mol) was added drop-wise and the mixture was stirred at room temperature for 16 hr. The mixture was diluted with hexanes, filtered through a pad of celite and rinsed with TMBE. The filtrate was concentrated to afford the title compound (16 g, 70%): 1H NMR (400 MHz, DMSO) delta 2.22 (s, 3H), 3.74 (s, 3H), 3.79 (s, 3H).

Provenance & Evidence