4-Bromopyridine → HCID 14171061, compound

Participants

Reaction Conditions

Reaction Steps

15.0 g. (0.095 mol) of 4-bromopyridine in 7 ml. of dry tetrahydrofuran (THF) was added dropwise at -70° C. to a solution of butyl lithium (1.6 M, 60.9 ml., 0.098 mol) dissolved in 120 ml. of dried THF over a ten minute period. The resulting very deep purple mixture was stirred at -70° C. for 30 minutes and then transferred by nylon tubing under positive nitrogen pressure into a stirred 0° C. solution of ethyl oxalate (55.2 g., 0.38 moles) in 90 ml. of dry THF. The solution was stirred at 0° C. for 45 minutes and then quenched by addition of 65 ml. glacial acetic acid. This was warmed to room temperature and poured into 500 ml. of water adjusted to pH 7.0 with saturated sodium bicarbonate and extracted with 3×200 ml. ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate filtered and concentrated to a brown oil. This oil was flash chromatographed on silica gel eluted with 1:2 ethyl acetate hexane. A viscous yellow oil was obtained; 5.8 g (34%), m/e 179, spectral data consistent with structure of title product.

Provenance & Evidence