Water → 5-Isopropylthiazole-4-carbaldehyde
Reaktionsgleichung
C[O:2][C:3]([C:5]1[N:6]=[CH:7][S:8][C:9]=1[CH:10]([CH3:12])[CH3:11])=O.CC(C[AlH]CC(C)C)C.O>C(Cl)Cl>[CH:10]([C:9]1[S:8][CH:7]=[N:6][C:5]=1[CH:3]=[O:2])([CH3:12])[CH3:11]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 6.8 g (37 mmol) of 5-isopropyl-thiazole-4-carboxylic acid methyl ester (J. Chem. Soc., Perkin Trans. 1, 1982:159-164) in CH2Cl2 (120 mL) was cooled to −78° C. under nitrogen and treated dropwise with DIBAL (37 mL of 1.0 M in CH2Cl2; 37 mmol). The mixture was stirred at low temperature for 45 minutes and then treated with another 20 mL of DIBAL. The solution was stirred for 1 hour at −78° C. H2O was added, and the mixture was extracted with EtOAc (3×150 mL). The combined extracts were washed with brine, dried (MgSO4), and concentrated. Chromatography of the residue over silica gel, eluting with 2:1 hexane:EtOAc, gave the title compound.