Sodium Hydroxide → 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

Participants

Reaction Steps

To a THF (60 mL) solution of sodium bis(2-methoxyethoxy)aluminum hydride (65% toluene solution, 56 mL), a THF (45 mL) solution of pyrrolidine (18 mL) was added dropwise for 15 minutes at −5° C. or less. The reaction solution was agitated at room temperature for 1 hour, a THF (15 mL) suspension of tert-butoxide (2.10 g) was added dropwise to the reaction solution at room temperature and the reaction mixture was agitated for 15 minutes. The reaction mixture was added dropwise to a THF (50 mL) solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzoic acid methyl ester (20 g) under ice-cooling for 30 minutes. The reaction mixture was agitated at room temperature for 2 hours and a 5N sodium hydroxide solution (150 mL) was added dropwise to the reaction solution. Ethyl acetate was added to the reaction solution and the organic layer was partitioned. The organic layer was washed with a saturated ammonium chloride solution and a saturated saline solution in this order. The organic layer was dried over anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure after filtration with a silica gel pad. The residue was diluted with ethyl acetate and the deposited solids were separated by filtering. 7.10 g of the title compound was obtained by air-drying the obtained solids overnight. Furthermore, crystallization mother liquid was concentrated under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate-2-propanol system), and 2.65 g of the title compound was obtained.

Provenance & Evidence