Sodium Chloride → 5-(Methoxycarbonyl)-4-methylthiophene-2-carboxylic acid

HRID 1952563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1952563
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:11]=[O:12])=[CH:8][C:9]=1[CH3:10])=[O:4].CC(=CC)C.[Cl-].[Na+].[O:20]1CCOCC1>O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]([OH:20])=[O:12])=[CH:8][C:9]=1[CH3:10])=[O:4]

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 105532-Methyl-2-buteneHCID 312751,4-DioxaneHCID 57618829Methyl 5-formyl-3-methylthiophene-2-carboxylate

Produkt 1

HCID 682266195-(Methoxycarbonyl)-4-methylthiophene-2-carboxylic acidAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 5-formyl-3-methyl-thiophene-2-carboxylic acid methyl ester (3.2 g, 17.4 mmol) in dioxane (20 ml) was added 2-methyl-2-butene (15 ml) and a solution of Na2ClO2 (4.71 g, 52.1 mmol) and NaH2PO4 (4.71 g, 39.2 mmol) in water (15 ml). The mixture was stirred at rt for 1 h. The solution was saturated with sodium chloride, then successively extracted with EtOAc and dichloromethane. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to afford the desired product (3.13 g, 90% yield)

Aufarbeitung

  1. extractionsuccessively extracted with EtOAc and dichloromethane
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b8f669c751c148ecba9fdd0b9e2907e8
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404859B2

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