Hydrochloric Acid → 10-Iodo-9-decenoic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of this 10-iodo-9-decenoate methyl ester (51.0 mg, 0.164 mmol, 1.0 eq.) in THF:H2O 3:1 (3.3 mL) was added LiOH (69.0 mg, 1.64 mmol, 10.0 eq.). The reaction was stirred at 50° C. for 4 h before diluting with Et2O (5 mL) and pouring into 1 M aqueous HCl (5 mL). The layers were separated and the aqueous layer was extracted with Et2O (3×5 mL). The combined organic layers were washed with brine (5 mL), dried over Na2SO4, and concentrated in vacuo. Purification of the crude product by flash chromatography (hexanes:EtOAc 5:1→EtOAc) provided 95 as a pale yellow solid (44.0 mg, 0.149 mmol, 91%). 1H NMR indicated an E:Z ratio of 10:1.

Provenance & Evidence