Benzyl Bromide → methyl 3-(benzyloxy)-2-thiophenecarboxylate

HRID 1611130Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1611130
[OH:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:11]([O:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5811273-Hydroxy-thiophene-2-carboxylic acid methyl ester

Produkt 1

HCID 2764114methyl 3-(benzyloxy)-2-thiophenecarboxylateAusbeute 100,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of methyl 3-hydroxy-2-thiophenecarboxylate (5.00 g, 31.61 mmol), benzyl bromide (3.76 mL, 31.61 mmol), and K2CO3 (4.81 g, 34.77 g) in acetone (50 mL) was stirred at reflux for 1.5 hrs. After cooled to room temperature, the mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=15/1 to 9/1) to give methyl 3-(benzyloxy)-2-thiophenecarboxylate as a pale yellow oil (7.91 g, yield: quant.).

Aufarbeitung

  1. temperatureat reflux for 1.5 hrs
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=15/1 to 9/1)

Quellen und Nachweise

ORD-Eintrag
ord-3e3816af37224e3d855890a70f0b2f71
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06984649B1

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