Ammonium Chloride → Ethyl (2e,4e,6e,10z,13z,16z,19z)-3-methyl-docosa-2,4,6,10,13,16,19-heptaenoate

Temperature

0 °C

A solution of triethyl 3-methyl-4-phosphono-2-butenoate (485 μl, 1.96 mmol) in a 5:1 mixture of anhydrous THF-DMPU (20 ml) was cooled to 0° C., and n-BuLi (2.5 M in hexane, 760 μl, 1.90 mmol) was added. The mixture was stirred for 0° C. for 20 min and then cooled to −78° C. A solution of (2E,6Z,9Z,12Z,15Z)-octadeca-2,4,6,10,13,16,19-pentaenal in THF (2 ml) was added, and the reaction mixture was stirred at −78° C. for an hour. The mixture was then allowed to warm to 0° C. during an hour. Then a saturated aqueous NH4Cl solution was added and the phases were separated. The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with water and dried (MgSO4). Evaporation of the solvents under reduced pressure followed by flash chromatography on silica:gel (95:5 hexane-EtOAc) gave the ester (120 mg).

1. temperaturecooled to −78° C
2. stirringthe reaction mixture was stirred at −78° C. for an hour
3. temperatureto warm to 0° C. during an hour
4. customthe phases were separated
5. extractionThe aqueous phase was extracted with ethyl acetate
6. washThe combined organic phases were washed with water
7. dry with materialdried (MgSO4)
8. customEvaporation of the solvents under reduced pressure

ORD record

ord-9bb8b2abc1ea4bf18d40aba37b7a0def

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08178708B2