Water → (+/-)-5-(1-Hydroxy-3,3-dimethyl-butyl)-thiophene-3-carboxylic acid methyl ester
Reaktionsgleichung
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([CH:10]=[O:11])[S:7][CH:6]=1)=[O:4].[CH2:12]([Mg]Cl)[C:13]([CH3:16])([CH3:15])[CH3:14].O>CCOCC>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([CH:10]([OH:11])[CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[S:7][CH:6]=1)=[O:4]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 5-formyl-thiophene-3-carboxylic acid methyl ester (0.504 g, 2.96 mmol) in Et2O (30 mL) at 0° C. is treated with neopentyl magnesium chloride (7.1 mL, 0.5 M in Et2O, 3.6 mmol) and stirred for 15 min. Solution warmed to rt and additional Et2O (10 mL) added. The reaction mixture is stirred overnight at rt. after which it is poured into H2O (30 mL) and extracted with EtOAc (3×50 mL). Combined extracts washed with brine, dried over MgSO4, filtered, and concentrated. The residue is loaded onto silica gel and eluted using hexanes with an ethyl acetate gradient from 0% to 50%. The resulting mixture is then loaded onto C18 and eluted using H2O and a MeCN gradient from 15% to 100% giving (±)-5-(1-hydroxy-3,3-dimethyl-butyl)-thiophene-3-carboxylic acid methyl ester (0.316 g, 44%) as a light yellow syrup.
Aufarbeitung
- stirringThe reaction mixture is stirred overnight at rt
- extractionextracted with EtOAc (3×50 mL)
- washCombined extracts washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- washeluted
- washeluted
Quellen und Nachweise
- ORD-Eintrag
- ord-3a8a0211ddc944c3829df023b285509b
- Quelldatensatz
- uspto-grants-2011_12
- Patentnummer
- US08084489B2
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