Water → 2-(2-Phenyl-4-thiazolylmethoxy)-5-pyridylmethanol

Participants

Reaction Steps

To a solution of 2-phenyl-4-thiazolylmethanol (6.69 g) and methyl 6-chloro-3-pyridinecarboxylate (6.01 g) in N,N-dimethylformamide (100 ml) was added sodium hydride (60% in oil, 1.40 g) at 0° C. and the mixture was stirred for 30 min. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. To a solution of the residue in tetrahydrofuran (150 ml) was added aluminum lithium hydride (1.33 g) at 0° C. and the mixture was stirred at room temperature for 10 min. Sodium sulfate 10 hydrate (11.3 g) was added to the reaction mixture and the mixture was stirred at room temperature for 30 min. The precipitate was filtered off and the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and 2-(2-phenyl-4-thiazolylmethoxy)-5-pyridylmethanol (5.81 g, yield 56%) was obtained as colorless crystals from a fraction eluted with tetrahydrofuran. The crystals were recrystallized from tetrahydrofuran-hexane. melting point: 134–135° C.

Provenance & Evidence