Water → 10-Iodo-9-decenoate methyl ester

Participants

Reaction Steps

To a suspension of CrCl2 (454 mg, 3.75 mmol, 7.0 eq.) in THF (1.5 mL) at 23° C. was added dropwise a solution of (E)-methyl 10-iododec-9-enoate (100 mg, 0.537 mmol, 1.0 eq.) and iodoform (422 mg, 1.07 mmol, 2.0 eq.) in dioxane (9.2 mL). After stirring for 12 h, the reaction mixture was diluted with Et2O (10 mL) and poured into water (10 mL). The layers were separated and the aqueous layer was extracted with Et2O (3×15 mL). The combined organic extracts were washed with brine (10 mL), dried over MgSO4, and concentrated in vacuo. Purification of the crude product by flash chromatography (hexanes→hexanes:EtOAc 9:1) provided 10-iodo-9-decenoate methyl ester as a yellow oil (105 mg, 0.337 mmol, 63%). 1H NMR indicated an E:Z ratio of 10:1.

Provenance & Evidence