Hydrochloric Acid → HCID 9927979, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl trans-4-chloro-2-isocyanocinnamate (step 4, 1.2 g, 5.1 mmol), tributyltin hydride (1.6 g, 5.6 mmol) and AIBN (43 mg, 0.26 mmol) in acetonitrile (30 ml) was heated at 100° C. After 1 h, tetrakis(triphenylphosphine)palladium (580 mg, 0.50 mmol) and benzoyl chloride (0.65 ml, 5.6 mmol) were added and the mixture was heated for a further 17 h. The mixture was cooled and poured into 2N aqueous HCl (50 ml) and extracted with diethyl ether (80 ml×2). The combined organic extracts were washed with saturated aqueous potassium fluoride (50 ml) and dried (MgSO4). After removal of solvent, the crude product was purified by flash column chromatography eluting with ethyl acetate/hexane (1:5) to afford 0.43 g (25%) of the title compound as white solids.

Provenance & Evidence