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-ee126b8fae80421bbf9b78f00d0288ef

Source dataset

uspto-grants-1993_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05202344