Hydrochloric Acid → HCID 178418646, Verbindung

HRID 5245

Reaktionsgleichung

Reaktionsgleichung von HRID 5245
[CH2:1]1[C:6](=[O:7])[O:5][CH2:4][C:2]1=[O:3].C(N(CC)CC)C.[ClH:15].CN(C)CCCN=C=NCC.C(O[C:34]1[CH:48]=[CH:47][C:37]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44](O)=[O:45])=[CH:36][CH:35]=1)CCCCC.Cl>CN(C)C1C=CN=CC=1.CCOCC>[OH:3][C:2]1[CH2:4][O:5][C:6](=[O:7])[C:1]=1[C:44](=[O:45])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][O:38][C:37]1[CH:47]=[CH:48][C:34]([Cl:15])=[CH:35][CH:36]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 521261Tetronic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 229027906-[4-(Hexyloxy)phenoxy]hexanoic acid

Produkt 1

HCID 178418646HCID 178418646, VerbindungAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a stirring solution of 554 mg (5.54 mmol) of tetronic acid in 20 mL of diemthylformamide is added 850 μL (6.09 mmol) of triethylamine and 220 mg (1.765 mmol) of 4-dimethylaminopyridine at 0° C. Next, 1.26 g (6.63 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 1.475 g (6.63 mmol) of 6-[4-(hexyloxy)phenoxy]hexanoic acid are added and the reaction mixture is stirred 2 days at room temperature. The reaction is acidified with 1.0N HCl and extracted three times with ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo giving a yellow solid. Pure material is obtained by trituration in ether, filtering to give 774 mg (43%) of 4-hydroxy-3-[6-(4-chlorophenoxy)-1-oxohexyl]-2(5H)-furanone.

Aufarbeitung

  1. extractionextracted three times with ether
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customgiving a yellow solid
  5. filtrationfiltering

Quellen und Nachweise

ORD-Eintrag
ord-3ef2cd7b916a450b941ab84417ba43f7
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242945

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