Triethylamine → Diethyl (t-Butyldimethylsiloxy)methylphosphonate

Participants

Reaction Steps

To a stirred solution of diethyl hydroxylmethylphosphonate (2.13 g, 12.7 mmol), triethylamine (2.12 ml, 15.2 mmol) and dimethylaminopyridine (77 mg, 0.63 mmol) in dichlormethane at 0° C. under argon, at r.t., was added t-butyldimethylsilyl chloride (1.85 g, 12.8 mmol) in dichloromethane (5 ml). After 14 hr the resulting slurry was poured into water (100 ml) and extracted with dichloromethane (2×100 ml). The organic extracts were dried (Na2SO4), concentrated in vacuo and the resulting oil chromatographed on silica gel eluted with ethylacetate:hexanes (1:1, v:v) to afford the title compound as a clear oil.

Provenance & Evidence