2-Ethylhexanoic Acid → HCID 23676231, compound

Participants

Reaction Steps

The product from step 1 (56 mg, 0.0961 mmol), triphenylphosphine (15 mg, 0.0577 mmol), 0.5M sodium 2-ethyl-hexanoate in ethyl acetate (0.211 mL, 0.106 mmol), 2-ethyl-hexanoic acid (0.0146 mL, 0.106 mmol), and tetrakis(triphenylphosphine)palladium(0) (22 mg, 0.0192 mmol) were combined in anhydrous dimethylfromamide (1 mL). The mixture was stirred at room temperature for 5 minutes, then cooled in an ice bath and stirred at 0-5° C. for 2 hours. The mixture was diluted with diethyl ether (12 mL) to precipitate a solid. The solid was collected by centrifugation, washed with ether (5 mL), and dried under vacuum. The solid was dissolved in water (5 mL) and added to a column (1×20 cm) of Amberchrom CG-161 resin. The column was eluted with water followed by a progressive gradient of acetonitrile in water. The product containing fractions were combined and lyophilized to a white, amorphous solid (18 mg). This material was further purified by preparative layer chromatography on a 1 mm×20 cm×20 cm RPSF plate, developing with 7:3 water-acetonitrile in an ice cooled tank. The product band was located by UV, removed and eluted with 4:1 acetonitrile-water. The eluent was washed with hexanes, filtered through a 0.45 micon disc, concentrated under vacuum to remove the acetonitrile, and lyophilized to afford the title compound (17.9 mg) as a white amorphous solid.

Provenance & Evidence