1,3-Propanediol → 1-(z,z,z,z,z,z-Docosa-4,7,10,13,16,19-hexaenoyloxy)-3-hydroxypropane

HRID 28304

Reaction equation

HRID 28304 reaction equation
[C:1]([OH:24])(=[O:23])[CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6]/[CH:7]=[CH:8]\[CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH3:22].[CH2:25](O)[CH2:26][CH2:27][OH:28].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:24][CH2:25][CH2:26][CH2:27][OH:28])(=[O:23])[CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6]/[CH:7]=[CH:8]\[CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 104421,3-PropanediolHCID 10868DicyclohexylcarbodiimideHCID 445580Doconexent

Product 1

HCID 867589511-(z,z,z,z,z,z-Docosa-4,7,10,13,16,19-hexaenoyloxy)-3-hydroxypropane

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

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.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. custompurified by flash chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ba77b7c555334b5fb024de271e85041c
Source dataset
uspto-grants-2008_09
Patent number
USRE040480E1

Linked notes

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