Toluene → (E,Z,E)-N-(2-Methylpropyl)-2,6,8-decatrienamide

30.2 g (180.5 mmol) of the triene carboxylic acid obtained in the above-mentioned Example B2(1) was dissolved in 90 ml of heptane and 12 ml of dimethylformamide (DMF), and 14.5 ml (1.1 eq) of thionyl chloride was added dropwise thereto by spending 1 hour, while stirring under ice-cooling. After completion of the dropwise addition and subsequent 1 hour of stirring, separation of liquid was carried out by adding 60 ml of water. A heptane solution of the thus obtained acid chloride was added dropwise to a mixture of 60 ml of toluene, 21.5 ml (1.2 eq) of isobutylamine and 30.2 ml (1.2 eq) of triethylamine, by spending 2 hours under ice-cooling, and after completion of the dropwise addition, stirring was carried out at room temperature for 2 hours. The organic layer was separated by adding 120 ml of water, and the organic layer was washed with 120 ml of 0.1 N NaOH aqueous solution and then washed twice with 120 ml of water. By subjecting the thus obtained organic layer to solvent evaporation under a reduced pressure, 35.3 g of the target spilanthol (yield 88%)

1. temperaturecooling
2. additionAfter completion of the dropwise addition and subsequent 1 hour
3. stirringof stirring
4. customseparation of liquid
5. additionby adding 60 ml of water
6. waitby spending 2 hours under ice-
7. temperaturecooling
8. additionafter completion of the dropwise addition
9. stirringstirring
10. waitwas carried out at room temperature for 2 hours
11. customThe organic layer was separated
12. additionby adding 120 ml of water
13. washthe organic layer was washed with 120 ml of 0.1 N NaOH aqueous solution
14. washwashed twice with 120 ml of water

ORD record

ord-841c06a6b2504f3eb97fe4ccefbc575a

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08217192B2