Hydrochloric Acid → HCID 54691689, compound

Participants

Reaction Steps

To a solution of n-pentyl amine (28.98 ml, 0.25 mol) in absolute EtOH (110 ml) was added ethyl crotonate (31.1 ml, 0.25 mol) and the solution was stirred for 16 h at room temperature. To the clear solution was then added diethyl oxalate (33.95 ml, 0.25 mol) followed by a solution of sodium ethoxide [freshly prepared from sodium (5.75 g, 0.25 mol) and 75 ml of absolute EtOH]. After stirring for 16 h at room temperature, the solvent was removed in vacuo to give an orange oil. Water was added to the oil followed by 1N HCl to acidify to pH=3, and the mixture was then extracted with CH2Cl2 (3×500 ml). The combined organic layers were washed with water and brine and then concentrated in vacuo to give an oil which was chromatographed on silica gel eluting with 10/89/1 EtOH/CH2Cl2 /HOAc to give the title compound (21.88 g, 34%) as a pink solid. DSC=37.8°-44.3° C. at 63.9 J/g.

Provenance & Evidence