Reaction #56589

Reaction equation

1,3-dicyclohexylcarbodiimide

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

4-phenylbutanoic acid

→

1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-(4-phenylbutanoyloxy)propane

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   FiltrationThe mixture was filtered
2. 2
   Concentrationconcentrated
3. 3
   Otherpurified by flash chromatography

Procedure

A solution of 1,3-dicyclohexylcarbodiimide (710 mg, 3.45 mmol) and 4-(N,N-dimethylamino)pyridine (475 mg, 3.9 mmol) in methylene chloride (10 ml) was added to a solution of 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane (1 g, 3 mmol) and 4-phenylbutanoic acid (520 mg, 3.15 mmol) in methylene chloride (15 ml). The resultant mixture was stirred at room temperature under nitrogen until it was complete as indicated by tlc. The mixture was filtered, concentrated and purified by flash chromatography to yield 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-(4-phenylbutanoyloxy)propane.

Source