Undecylenic Acid → HCID 72546827, compound

Participants

Reaction Steps

An oven-dried, 25 mL one-necked round-bottomed flask was charged with compound 15b (0.021 g, 0.060 mmol), DCC (0.014 g, 0.069 mmol), DMAP (0.008 g, 0.069 mmol) and dry CH2Cl2 (7 mL). 10-Undecenoic acid (0.012 mL, 0.060 mmol) was added and the mixture was stirred at rt overnight. The consumption of the starting material was monitored by TLC (AcOEt/n-hexane 1:9). After filtration over a short pad of celite, the reaction was quenched with sat'd aq NaHCO3 solution (30 mL). The layers were separated and the aqueous phase was extracted with Et2O (3×15 mL). The combined organic layers were washed with brine (2×40 mL), dried over MgSO4, gravity filtered, and concentrated under reduced pressure. The reaction residue was purified by silica gel flash chromatography, eluting with AcOEt/n-hexane 1.5:8.5, to provide 0.018 g of the title compound as a yellow solid in 60% yield.

Provenance & Evidence