Ethyl Acetate → 5-Hydroxymethyl-2-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-propyl]-1,2,4-triazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-carbomethoxy-2-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-propyl]-1,2,4-triazole (37.1 mg, 0.1 mmol) in 1 ml of THF was added at 0° C. a solution of 1M LAH in THF (65 μl, 1M in THF, 0.065 mmol). The mixture was stirred for 10 min at 0° C. and then stirred at 20° C. for 24 h. Rochelle salt solution was added to the mixture and the solution was stirred at 20° C. for 10 min. Ethyl acetate was added to the above mixture, the aqueous layer was extracted with methylene chloride (3×), and the combined organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica column chromatography (10 cm column, ethyl acetate/hexane, 1/1 - 1/0; methylene chloride/acetone, 2/1 - 1/2) to afford 27 mg (79%) of 5-hydroxymethyl-2-[3-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-propyl]-1,2,4-triazole, as a white solid.

Provenance & Evidence