1,2-Dichloroethane → {4-[4-(Pyrrolidin-1-ylcarbonyl)-1,3-oxazol-2-yl]phenyl}methanol

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 2-[4-(hydroxymethyl)phenyl]-1,3-oxazole-4-carboxylic acid (0.99 g, 4.5 mmol) in DMF was treated sequentially with EDC (1.04 g, 5.4 mmol), HOBt (0.67 g, 5.0 mmol and pyrrolidine (0.35 g, 5.0 mmol), stirred at 80° C. for 4 hours and evaporated to dryness. The resultant residue was dissolved in EtOAc and water. The layers were separated and the organic layer was washed successively with 1M HCl, water, saturated NaHCO3 and brine, dried over Na2SO4 and concentrated under reduced pressure The resultant residue was purified by flash chromatography (silica, EtOAc:hexanes 25%) to give the title product in 84% yield, identified by NMR and mass spectral analyses. LCMS (ESI+) 273 (MH+).

Provenance & Evidence