Dimethylformamide → HCID 69679890, compound

Participants

Reaction Conditions

Reaction Steps

3-Methoxymethoxypyridine (17.5 g, 130 mmol) is dissolved in THF (500 ml), and thereto is added a solution of n-butyl lithium in hexane (88 ml, 140 mmol) at −30° C. The mixture is stirred at 0° C. for 20 minutes, and cooled to −70° C. To the mixture is added DMF (11.0 g, 150 mmol), and the mixture is stirred again at 0° C. for 30 minutes. Then, thereto is added a solution of a salt which is prepared from triethylphosphonoacetate (34.0 g, 150 mmol) and sodium hydride (60% in mineral oil, 6.0 g, 150 mmol) in THF (200 ml) at 0° C., and the mixture is stirred for one hour. The reaction solution is poured into ice-water, extracted with ethyl acetate (400 ml×2), and the residue is purified by silica gel column chromatography (eluent: ethyl acetate/hexane) to give the title compound (22.0 g) as pale yellow oil.

Provenance & Evidence