Water → 10-Iodo-9-decenoate methyl ester

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.

1. customThe layers were separated
2. extractionthe aqueous layer was extracted with Et2O (3×15 mL)
3. washThe combined organic extracts were washed with brine (10 mL)
4. dry with materialdried over MgSO4
5. concentrationconcentrated in vacuo
6. customPurification of the crude product by flash chromatography (hexanes→hexanes:EtOAc 9:1)

ORD record

ord-0c1f5a720fb0465f8f79c9f86cf8dab4

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08013203B2