Acetonitrile → HCID 87508366, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl isocyanoacetate (4.29 g, 37.9 mmol) in anhydrous ACN (400 mL) is added anhydrous K2CO3 (K2SO4, 31.4 g, 227 mmol), TBAHS (tetrabutyl ammonium hydrogen sulfate, 2.57 g, 7.58 mmol), and 1,2-bis-bromomethyl-benzene (10.0 g, 37.9 mmol). The resulting heterogeneous mixture is stirred at 75° C. overnight. The reaction mixture is cooled down to RT and filtered to remove the unwanted salts. The filter cake is washed with ACN (20 mL) and the filtrate is concentrated in vacuo. The residue is dissolved in ethyl ether (150 mL) and washed with water (1×10 mL) and brine (3×10 mL). The organic layer is dried over Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (400 g silica gel; gradient elution: 20-100% EtOAc in heptane) to give a pure product as white solid (8.0 g, 49%).

Provenance & Evidence