Hydrochloric Acid → HCID 54691689, compound

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.

1. stirringAfter stirring for 16 h at room temperature
2. customthe solvent was removed in vacuo
3. customto give an orange oil
4. extractionthe mixture was then extracted with CH2Cl2 (3×500 ml)
5. washThe combined organic layers were washed with water and brine
6. concentrationconcentrated in vacuo
7. customto give an oil which
8. customwas chromatographed on silica gel eluting with 10/89/1 EtOH/CH2Cl2 /HOAc

ORD record

ord-e165ada10ff747f39f19e7813a919843

Source dataset

uspto-grants-1994_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05314886