Reacción #56579

ord-12e1b6c647304b9a9fbd0f57e4f2eb63

Ecuación de reacción

C(=NC1CCCCC1)=NC1CCCCC1
1,3-dicyclohexylcarbodiimide
CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)OCCCO
1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane
CCCCCCCC/C=C\CCCCCCCC(=O)O
z-octadeca-9-enoic acid
CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)OCCCOC(=O)CCCCCCC/C=C\CCCCCCCC
1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-(z-octadeca-9-enoyloxy)propane

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroOn completion of reaction
  2. 2
    Filtraciónfiltered
  3. 3
    Concentraciónconcentrated
  4. 4
    Otropurified
  5. 5
    Otroby dry column chromatography

Procedimiento

A solution of 1,3-dicyclohexylcarbodiimide (23.7 g) and 4-(N,N-dimethylamino)pyridine (15.9 g) in methylene chloride (200 ml) was added to a solution of 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane (33.6 g) and z-octadeca-9-enoic acid (30 g) in methylene chloride (400 ml) under nitrogen at room temperature. On completion of reaction as evidenced by tic analysis the solution was diluted with hexane, filtered, concentrated and purified by dry column chromatography to yield 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-(z-octadeca-9-enoyloxy)propane as a free flowing pale yellow oil.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: USRE040480E1uspto-grants-2008_09