1,3-Propanediol → 1-(z,z,z-Octadeca-6,9,12-trienoyloxy)-3-hydroxypropane

HRID 1268421Notes

Reaction equation

HRID 1268421 reaction equation
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[OH:21][CH2:22][CH2:23][CH2:24]O.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:20][CH2:24][CH2:23][CH2:22][OH:21])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 104421,3-PropanediolHCID 10868DicyclohexylcarbodiimideHCID 5280933Gamma-Linolenic acid

Product 1

HCID 103371121-(z,z,z-Octadeca-6,9,12-trienoyloxy)-3-hydroxypropane

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of z,z,z-octadeca-6,9,12-trienoic acid (150 g) in methylene chloride (500 ml) was added dropwise to a mixture of 1,3-dihydroxypropane (205 g), 1,3-dicyclohexylcarbodiimide (130 g) and 4-(N,N-dimethylamino)pyridine (87 g) in methylene chloride (2500 ml) at room temperature under nitrogen. When tlc indicated that the reaction had gone to completion the reaction mixture was filtered. The filtrate was washed with dilute hydrochloric acid, water and saturated sodium chloride solution. The solution was dried, concentrated and purified by dry column chromatography to yield 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-hydroxypropane as a pale yellow oil.

Workup

  1. filtrationwas filtered
  2. washThe filtrate was washed with dilute hydrochloric acid, water and saturated sodium chloride solution
  3. customThe solution was dried
  4. concentrationconcentrated
  5. custompurified
  6. customby dry column chromatography

Sources & evidence

ORD record
ord-22306e1e2c224838b9e56104ecd27b1e
Source dataset
uspto-grants-2003_04
Patent number
US06555700B1

Reaction notes

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