Citric Acid → 5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1,3-thiazole-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1,3-thiazole (7.44 g) in tetrahydrofuran (100 mL) was slowly added a 1.6M n-butyllithium hexane solution (25.6 mL) at −70° C. under a nitrogen atmosphere. The reaction mixture was stirred at −70° C. for 30 min and N,N-dimethylformamide (8.0 g) was added. The reaction mixture was warmed to room temperature, 10% aqueous citric acid solution was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (6.91 g, yield 82%) was obtained as a yellow oil from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio). MS: 228 (MH+).

Provenance & Evidence