Water → Methyl 5-(1-hydroxy-2-methylpropan-2-yl)thiophene-2-carboxylate

HRID 660985Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 660985
[OH:1][CH2:2][C:3]([C:6]1[S:10][C:9]([C:11]([OH:13])=[O:12])=[CH:8][CH:7]=1)([CH3:5])[CH3:4].[C:14]([O-])([O-])=O.[K+].[K+].IC.O>CN(C=O)C>[CH3:14][O:12][C:11]([C:9]1[S:10][C:6]([C:3]([CH3:4])([CH3:5])[CH2:2][OH:1])=[CH:7][CH:8]=1)=[O:13]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 674845155-(2-Hydroxy-1,1-dimethyl-ethyl)-thiophene-2-carboxylic acid

Produkt 1

HCID 67484466Methyl 5-(1-hydroxy-2-methylpropan-2-yl)thiophene-2-carboxylateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 5-(2-hydroxy-1,1-dimethyl-ethyl)-thiophene-2-carboxylic acid (0.495 g, 2.47 mmol) in DMF (12.0 mL) is treated with K2CO3 (0.515 g, 3.73 mmol), iodomethane (0.23 mL, 3.69 mmol), and stirred at rt overnight. The mixture is poured into H2O (25 mL) and extracted with EtOAc (3×25 mL). The combined extracts are washed with H2O, brine, dried over MgSO4, filtered, and concentrated. The residue is loaded onto silica gel and eluted with hexanes using a gradient of 0% to 75% EtOAc to give 5-(2-hydroxy-1,1-dimethyl-ethyl)-thiophene-2-carboxylic acid methyl ester (0.439 g, 83%). MS (ES): 215.1 [M+H]+.

Aufarbeitung

  1. extractionextracted with EtOAc (3×25 mL)
  2. washThe combined extracts are washed with H2O, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washeluted with hexanes using a gradient of 0% to 75% EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-aa43d418331a42d69b5c453c0988f090
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084489B2

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