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

HRID 1268425

Reaktionsgleichung

Reaktionsgleichung von HRID 1268425
[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]

Komponenten

6

Edukt 3

HCID 104421,3-PropanediolHCID 10868DicyclohexylcarbodiimideHCID 445580Doconexent

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-cc3cd4cd7fa243478e0ded370ee2c295
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06555700B1

Verknüpfte Notizen

Wird geladen…