Furan → 1-Oxo-1-furyl-7-methoxycarbonyl-4-heptyne

HRID 1612995

Reaktionsgleichung

Reaktionsgleichung von HRID 1612995
[CH3:1][O:2][C:3]([CH2:5][CH2:6][C:7]#[C:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[O:4].[O:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[OH-].[Na+]>ClCCl>[O:13]=[C:11]([C:15]1[O:14][CH:18]=[CH:17][CH:16]=1)[CH2:10][CH2:9][C:8]#[C:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4]

Komponenten

6

Edukt 4

HCID 8029FuranHCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 109761516-Methoxycarbonyl-1-carboxy-3-hexyne

Produkt 1

HCID 110208121-Oxo-1-furyl-7-methoxycarbonyl-4-heptyneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 6-methoxycarbonyl-1-carboxy-3-hexyne [VI-1] (27.6 g, 0.15 mole), furan (30.7 g, 0.45 mole) and dichloromethane (150 ml) is added trifluoroacetic anhydride (37.8 g, 0.18 mole) at room temperature, and the mixture is reacted at 30°-35° C. for 24 hours. After completion of the reaction, the reaction solution is poured into ice-water and neutralized with 20% aqueous sodium hydroxide solution. The organic layer is separated and washed successively with 5% aqueous sodium hydrogen carbonate solution and water. The organic layer is concentrated under reduced pressure to give 1-oxo-1-furyl-7-methoxycarbonyl-4-heptyne [VII-1] (32.3 g, yield; 92%).

Aufarbeitung

  1. customthe mixture is reacted at 30°-35° C. for 24 hours
  2. customAfter completion of the reaction
  3. customThe organic layer is separated
  4. washwashed successively with 5% aqueous sodium hydrogen carbonate solution and water
  5. concentrationThe organic layer is concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b61e2a66f6604740a7874d7be8fc8165
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05191109

Verknüpfte Notizen

Wird geladen…