Diethyl Ether → (2-Cyclopropylthiazol-4-yl)methanol

Participants

Reaction Steps

To a mixture of lithium aluminium hydride (0.32 g) and anhydrous ether (40 ml) was added dropwise an anhydrous ether (10 ml) solution of ethyl 2-cyclopropyl-4-thiazolecarboxylate (1.65 g), followed by stirring for one hour at room temperature. To the reaction mixture was added dropwise water (20 ml) under cooling with ice to decompose excess amount of the reducing agent. To the resultant mixture were added ethyl acetate (50 ml) and water (25 ml), followed by extraction with ethyl acetate. The organic layer was washed with water (25 ml) and a saturated aqueous solution of sodium chloride (25 ml), successively, followed by drying over magnesium sulfate. The solvent was distilled off, and the residue was subjected to a silica gel chromatography (2.5×30 cm), eluting with ethyl acetate-hexane (2:1). The desired fraction was concentrated to give 2-cyclopropyl-4-hydroxymethyl thiazole (0.94 g) as pale yellow needles. 1H-NMR (CDCl3) δ: 0.98~1.18(4H,m), 2.24~2.39(1H,m), 3.20(1H,bs.), 4.70(2H,d,J=5 Hz), 6.93(1H,s)

Provenance & Evidence