Ethyl isocyanoacetate → HCID 20037383, compound

Participants

Reaction Steps

To a slurry of potassium t-butoxide (4.48 g, 40 mmol) in dry, distilled tetrahydrofuran (40 mL) in a 3-neck 250 mL flask at -78° C., under argon was added dropwise from an addition funnel a solution of ethyl isocyanoacetate (4.52 g, 40 mmol) in dry, distilled tetrahydrofuran (40 mL). The anion was allowed to form for 25 min at -78° C., then solid bis(dimethylamino)ethoxymethylium tetrafluoroborate [9.28 g, 40 mmol, prepared as described by von H. Meerwein, W. Florian, N. Schon, G. Stopp, Justus Liebigs Ann. Chem. 641, 1, (1960)] was added as quickly as possible through a powder funnel with a stream of argon. The reaction was allowed to warm to ambient temperature and stir for 4 hours. It was then poured onto water (200 mL) and saturated ammonium chloride (40 mL) and extracted three times with ethyl acetate (100 mL). The combined extracts were washed with water and saturated sodium chloride, dried over sodium sulfate, and the solvent removed under reduced pressure. The resulting brown oil (6.9 g) was flash chromatographed, eluting with ethyl acetate, to give slightly impure D-36a as a brown oil (4.78 g, 57%). It was used without further purification

Provenance & Evidence