2-Ethylhexanoic Acid → HCID 23665175, compound

Participants

Reaction Steps

The product from step 1 (29 mg, 0.055 mmol), triphenylphosphine (6.3 mg, 0.024 mmol), 0.5M sodium 2-ethyl-hexanoate in ethyl acetate (0.125 mL, 0.063 mmol), and 2-ethyl-hexanoic acid (0.0098 mL, 0.061 mmol) were dissolved in 1:1 dichloromethane-ethyl acetate (1 mL). Tetrakis(triphenylphosphine)palladium(0) (7 mg, 0.0061 mmol) was added and the resulting mixture was stirred at room temperature for 30 minutes. The mixture was diluted with diethyl ether (7 mL) and extracted with water (2×1.5 mL). The aqueous extracts were washed with hexanes, concentrated under vacuum, and purified by preparative layer chromatography on a 1 mm×20 cm×20 cm RPSF plate, using 3:1 water-acetonitrile as the developing solvent. The product band was located by UV, removed and eluted with 4:1 acetonitrile-water. The eluent was concentrated under vacuum to remove the acetonitrile and lyophilized to afford the crude product (11 mg). This material was dissolved in ice cold water (1.5 mL) and applied to a small column of Amberchrom CG-161 resin (5 mm×5 cm). The column was eluted with cold water (20 mL) followed by 20% aqueous isopropanol in 2 mL fractions. The product containing, aqueous isopropanol fractions (2-7) were combined, concentrated under vacuum, and lyophilized to afford the title compound (5.6 mg) as an amorphous solid.

Provenance & Evidence