Phosphate → Methyl 3-(hydroxymethyl)thiophene-2-carboxylate

HRID 1766946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1766946
C([O:4][CH2:5][C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([O:13][CH3:14])=[O:12])(=O)C.C(=O)([O-])[O-].[K+].[K+].P([O-])([O-])([O-])=O>CO>[OH:4][CH2:5][C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([O:13][CH3:14])=[O:12]

Komponenten

5

Edukt 3

HCID 1061PhosphateHCID 11430Potassium CarbonateHCID 17862579Methyl 3-(acetoxymethyl)-2-thenoate

Produkt 1

HCID 17862582Methyl 3-(hydroxymethyl)thiophene-2-carboxylateAusbeute 100,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of methyl 3-(acetoxymethyl)-2-thenoate (4.89 g, 22.8 mmol) obtained from Example 37-(1) in methanol (60 ml) was added potassium carbonate (157.7 mg, 1.14 mmol), and the mixture was stirred at room temperature for 1 hour. A phosphate buffer solution (pH 7, 20 ml) was added to the reaction mixture, and the methanol was evaporated under reduced pressure. The product was extracted with ethyl acetate, and then the solvent was evaporated under reduced pressure. The obtained oily residue was subjected to chromatography on a silica gel (90 g) column (eluent; ethyl acetate:hexane=1:2) to give the title compound (3.94 g, quantitative yield) as needle crystals (mp. 35-36° C.).

Aufarbeitung

  1. customthe methanol was evaporated under reduced pressure
  2. extractionThe product was extracted with ethyl acetate
  3. customthe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b0fd08d56b224158846ce7745bde4b0e
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07230023B2

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