Methyl 4-(5-formyl-2-thienyl)benzoate → 4-(5-Hydroxymethyl-thiophen-2-yl)benzoic acid methyl ester

HRID 45905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 45905
[BH4-].[Na+].[CH3:3][O:4][C:5](=[O:19])[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([CH:17]=[O:18])=[CH:15][CH:16]=2)=[CH:8][CH:7]=1>CO.ClCCl>[CH3:3][O:4][C:5](=[O:19])[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([CH2:17][OH:18])=[CH:15][CH:16]=2)=[CH:8][CH:7]=1

Komponenten

4

Edukt 2

HCID 2763348Methyl 4-(5-formyl-2-thienyl)benzoateHCID 4311764Sodium borohydride

Produkt 1

HCID 667422984-(5-Hydroxymethyl-thiophen-2-yl)benzoic acid methyl esterAusbeute 78,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

Sodium borohydride (155 mg, 4.1 mmol) is added to a solution of 4-(5-formylthiophen-2-yl)benzoic acid methyl ester (1.01 g, 4.1 mmol) in methanol/dichloromethane (16 ml/4 ml) and the resulting solution is stirred for 90 minutes at room temperature. The reaction is quenched by the addition of saturated aqueous ammonium chloride solution (100 ml) and extracted with dichloromethane (100 ml). The organic layer is washed with brine, dried over magnesium sulphate, filtered and concentrated in vacuo to give 4-(5-hydroxymethyl-thiophen-2-yl)benzoic acid methyl ester (800 mg)

Aufarbeitung

  1. customThe reaction is quenched by the addition of saturated aqueous ammonium chloride solution (100 ml)
  2. extractionextracted with dichloromethane (100 ml)
  3. washThe organic layer is washed with brine
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1910b5ea421846269123ae5f8f2493ac
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541594B2

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