Ethyl isobutyrate → HCID 19854762, compound

Participants

Reaction Conditions

Reaction Steps

1.5M Butyllithium in hexane (20 ml) was added dropwise, under argon, to a stirred, cooled (-20° C.) solution of diisopropylamine (4.2 ml) in THF (50 ml). After 10 minutes the mixture was cooled to -70° C. and ethyl isobutyrate (3.99 ml) was added dropwise keeping the temperature <-60° C. Stirring was continued for 20 minutes after completion of the addition then DMPU (15 ml) was added followed by solid 3-chloromethylpyridine hydrochloride (2.0 g). After stirring for 30 minutes at -70° C., the mixture was allowed to warm to 4° C. and was then added to saturated ammonium chloride solution (200 ml). The mixture obtained was extracted with ether (3×100 ml). The combined extracts were washed with brine (50 ml), dried (MgSO4) and evaporated. The residue was purified by flash chromatrography using ether as eluant to give ethyl 3-(3-pyridyl)-2,2-dimethylpropionate (A) as a clear oil (2.12 g); NMR (CDCl3): 1.20 (6H, s), 1.23 (3H, t J=7 Hz), 2.87 (2H, s), 4.12 (2H, q J=7 Hz). 7.20 (1H, J=7, 5 Hz), 7.46 (1H, dt J=7, 1 Hz), 8.40 (1H, d J=1.5 Hz), 8.47 (1H, dd J=5, 1.5 Hz).

Provenance & Evidence