Sodium Iodide → (Z)-11-Hexadecenyl acetate

Temperature

0 °C

This example is designed to produce Z-11-hexadecenyl acetate through the reaction shown in FIG. 3. To a dry 50-mL round-bottomed flask is added 4.5 g (0.026 mol) 7-octenyl acetate, 3.3 g (0.026 mol) 1,2-epoxy-5-cyclooctene and a magnetic stir bar. The solution is cooled to 0° C. and sparged with nitrogen for 10 minutes. Grubbs catalyst 848 (1.10 g, 1.30 mmol) is added and the reaction is stirred at 0° C. for 24 hours. The reaction is quenched by addition of 15 ml of 2M THP in IPA solution, warmed to 60° C. with stirring for 24 hours. Water (5 mL) is added and stirred vigorously for 10 minutes. The aqueous layer is separated, and the product washed with brine solution and dried over sodium sulfate. The product is purified by vacuum distillation, and then hydrogenated using 10% palladium on carbon (Pd/C) with a 5 psi overpressure of hydrogen. The catalyst is filtered off without further purification. The epoxide is converted to the cis olefin as described in (Tetrahedron Lett. 22, 3551 (1981)). There is sufficient detail to run the reaction 11,12-Epoxy-hexadecyl acetate is treated with 2.87 g (0.026 mol) chlorotrimethylsilane and 3.96 g (0.026 mol) sodium iodide. The reaction is slowly heated from room temperature to 60° C., until the starting materials are consumed. The mixture is then quenched with water and the organic phase was washed with an aqueous solution of sodium bicarbonate, and finally water. The organic phase is dried over sodium sulfate, acetylated with acetic anhydride and acetic acid and vacuum distilled to yield Z-11-hexadecenyl acetate.

1. customsparged with nitrogen for 10 minutes
2. customThe reaction is quenched by addition of 15 ml of 2M THP in IPA solution
3. temperaturewarmed to 60° C.
4. stirringwith stirring for 24 hours
5. additionWater (5 mL) is added
6. stirringstirred vigorously for 10 minutes
7. customThe aqueous layer is separated
8. washthe product washed with brine solution
9. dry with materialdried over sodium sulfate
10. distillationThe product is purified by vacuum distillation
11. filtrationThe catalyst is filtered off without further purification
12. customthe reaction 11,12-Epoxy-hexadecyl acetate
13. temperatureThe reaction is slowly heated from room temperature to 60° C., until the starting materials
14. customare consumed
15. customThe mixture is then quenched with water
16. washthe organic phase was washed with an aqueous solution of sodium bicarbonate, and finally water
17. dry with materialThe organic phase is dried over sodium sulfate
18. distillationdistilled

ORD record

ord-7194a23e78614ff9866b1b9cd4fb92a9

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06900347B2