tert-Butyl diethylphosphonoacetate → HCID 67114131, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of sodium tert-butoxide (7.63 g, 79.4 mmol) in 1,2-dimethoxyethane (70 mL) at ambient temperature was added tert-butyl diethylphosphonoacetate (20.0 g, 79.4 mmol) over 30 minutes, then allowed to stir a further 40 minutes then 3-(oxiran-2-yl)pyridine (4.8 g, 39.7 mmol) was added drop wise. The suspension was stirred at for 30 minutes then heated to 65° C. overnight. The reaction was poured onto ice and extracted with diethyl ether. The combined organic extracts were washed with saturated aqueous sodium chloride, dried (MgSO4), and evaporated to provide an orange oil which was purified by flash chromatography (elution solvent: 20% (v/v) hexane/dichloromethane) to obtain 3.0 g of purified material.

Provenance & Evidence