Hexamethylphosphoramide → cis-5-(11-Tetradecenyloxy)furancarboxylic acid

HRID 1111411

Reaktionsgleichung

Reaktionsgleichung von HRID 1111411
[CH2:1]([OH:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH3:14].[OH-].[Na+].Cl[C:19]1[O:23][C:22]([C:24]([OH:26])=[O:25])=[CH:21][CH:20]=1.CN(C)P(=O)(N(C)C)N(C)C>C1(C)C=CC=CC=1.C(O)(=O)C>[CH2:1]([O:15][C:19]1[O:23][C:22]([C:24]([OH:26])=[O:25])=[CH:21][CH:20]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH3:14]

Komponenten

7

Edukt 4

HCID 12679HexamethylphosphoramideHCID 14798Sodium HydroxideHCID 2348535-Chlorofuran-2-carboxylic acidHCID 1712010Cis-11-tetradecenol

Produkt 1

HCID 13655994cis-5-(11-Tetradecenyloxy)furancarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

8.8 g (0.0414 mole) of cis-11-tetradecen-1-ol was combined with 4.0 g (0.0829 mole) of sodium hydroxide (50% in oil) in 200 ml of dry toluene and heated to reflux with stirring for 3 hours. 6.1 g (0.414 mole) of 5-chloro-2furoic acid was added, followed by 25 ml of hexamethylphosphoric triamide (HMPA), and the reaction mixture refluxed with stirring for 20 hours, cooled, and acidified with acetic acid. The mixture was extracted into ether and the organic layer washed with water and with brine and evaporated to yield cis-5-(11-tetradecenyloxy)furan-2-carboxylic acid, M.P. 89°-90° C.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux
  3. temperaturethe reaction mixture refluxed
  4. stirringwith stirring for 20 hours
  5. temperaturecooled
  6. extractionThe mixture was extracted into ether
  7. washthe organic layer washed with water and with brine
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2fde1a579fce4f309cd39843c06b6e6b
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04980371

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