Dicyclohexylcarbodiimide → Retinal

HRID 346880

Reaktionsgleichung

Reaktionsgleichung von HRID 346880
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:22])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:21])=[CH:17]/[C:18](O)=[O:19].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C.CC1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/CO>ClCCl.CCCCCC.C(OCC)C>[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:8])([CH3:9])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:22])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:21])=[CH:17]/[CH:18]=[O:19]

Komponenten

7

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 444795Retinoic AcidHCID 445354Retinol

Produkt 1

HCID 638015RetinalAusbeute 129,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 21584099Diethylether hexaneLösungsmittel

Versuchsvorschrift

Retinoic acid (1.26 g, 0.0042 mol, Basf Co.), dicyclohexylcarbodiimide (DCC) (0.87 g, 0.0042 mol) and catalytic amount of dimethylaminopyridine (DMAP) were added to retinol (1.00 g, 0.0035 mol) dissolved in anhydrous dichloromethane (50 ml) at 0° C. The reaction solution was slowly warmed to room temperature and stirred for 12 hours under nitrogen atmosphere and under the condition for light and moisture to be intercepted. The reaction solution was filtered and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (silica gel 60 for cc part, Merk Co., mesh size 270–400, hexane/diethylether=19/1, v/v) to give 1.55 g (Yield 78%) of the pale yellow title compound.

Aufarbeitung

  1. filtrationThe reaction solution was filtered
  2. customthe solvent was removed by distillation under reduced pressure
  3. customThe residue was purified by column chromatography (silica gel 60 for cc part, Merk Co

Quellen und Nachweise

ORD-Eintrag
ord-9eb3a1f1fd5e4d55865230379739028c
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173062B2

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