Water → Methyl 5-methyl-2-furancarboxylate

HRID 514881

Reaktionsgleichung

Reaktionsgleichung von HRID 514881
[O:1]1[CH:5]=C[CH:3]=[CH:2]1.[CH2:6]1[CH2:16][CH2:15]N2[C:9](=NCCC2)[CH2:8][CH2:7]1.[O:17]1CCCC1.[OH2:22]>>[CH3:15][C:16]1[O:22][C:8]([C:9]([O:1][CH3:5])=[O:17])=[CH:7][CH:6]=1.[CH3:15][C:16]1[O:22][C:8]([C:9]([O:1][CH2:2][CH3:3])=[O:17])=[CH:7][CH:6]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 8029Furan3×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Produkt 2

HCID 137628Methyl 5-methyl-2-furancarboxylateHCID 50630802-Furancarboxylic acid, 5-methyl-, ethyl ester

Versuchsvorschrift

The method of the present invention involves preparing furan-containing molecules of formula I, which are useful chemical building blocks and fuel or fuel additives, from furan-containing molecules of formula II, in greater than 50% yield. The first step involves contacting a furan-containing molecule of formula II, a base, such as DBU, an organic solvent, such as tetrahydrofuran (THF), a catalyst, such as an N-heterocyclic carbene, and a reactive nucleophile, such as alcohols, water, amines or thiols, in a reaction vessel at a temperature of from about −78 degree C. to 150 degree C. After completion, the second step involves separating the product molecules of formula I by extraction with a hydrophobic solvent, such as ethyl acetate. The yield to methyl 5-methyl-2-furoate and ethyl 5-methyl-2-furoate are greater than 70% by this method.

Aufarbeitung

  1. additioncontaining molecules of formula I, which
  2. customof from about −78 degree C
  3. customto 150 degree
  4. customAfter completion, the second step involves separating the product molecules of formula I
  5. extractionby extraction with a hydrophobic solvent

Quellen und Nachweise

ORD-Eintrag
ord-e1ff273691b046ecb730a7349ecdfc8b
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108940B2

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