Reaction #56582

Reaction equation

z,z,z,z,z,z-docosa-4,7,10,13,16,19-hexaenoic acid

1,3-propane diol

1,3-dicyclohexylcarbodiimide

→

1-(z,z,z,z,z,z-docosa-4,7,10,13,16,19-hexaenoyloxy)-3-hydroxypropane

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   FiltrationThe reaction was filtered
2. 2
   Concentrationconcentrated
3. 3
   Otherpurified by flash chromatography (ethyl acetate/hexane)

Procedure

A solution of z,z,z,z,z,z-docosa-4,7,10,13,16,19-hexaenoic acid (6.4 g, 19.5 mmol) in methylene chloride (225 ml) was added dropwise to a solution of 1,3-propane diol (7.5 g, 99 mmol), 1,3-dicyclohexylcarbodiimide (4.65 g, 20 mmol) and 4-(N,N-dimethylamino)pyridine (2.1 g, 17 mmol) in methylene chloride (225 ml) at −10° C. The reaction mixture was stirred overnight, warming up to room temperature. The reaction was filtered, concentrated and purified by flash chromatography (ethyl acetate/hexane) to yield 1-(z,z,z,z,z,z-docosa-4,7,10,13,16,19-hexaenoyloxy)-3-hydroxypropane as a pale yellow oil.

Source