Reaction #56579

Reaction equation

1,3-dicyclohexylcarbodiimide

1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane

z-octadeca-9-enoic acid

→

1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-(z-octadeca-9-enoyloxy)propane

Solvents

hexane

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   OtherOn completion of reaction
2. 2
   Filtrationfiltered
3. 3
   Concentrationconcentrated
4. 4
   Otherpurified
5. 5
   Otherby dry column chromatography

Procedure

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.

Source