Triphenylphosphine → methyl [3-[2-[5-(diphenylmethyl)-2H-tetrazol-2-yl]ethyl]phenoxy]acetate

Participants

Reaction Conditions

Reaction Steps

Diethyl azodicarboxylate (0.96 g, 5.5 mmol) was added to a stirred solution of 5-(diphenylmethyl)-2H-tetrazole (1.00 g, 4.2 mmol), methyl [3-(2-hydroxyethyl)phenoxy]acetate (0.98 g, 4.6 mmol) and triphenylphosphine (1.44 g, 5.5 mmol) in dry THF (17 mL) cooled to 0° C. in an ice bath. The ice bath was removed and the mixture stirred at room temperature for 1 hour before the solvent was evaporated. The residue was chromatographed on a column of silica gel using a mixture of hexanes and ethyl acetate (3:1) to give methyl [3-[2-[5-(diphenylmethyl)-2H-tetrazol-2-yl]ethyl]phenoxy]acetate (1.06 g, 58%) as a colorless oil.

Provenance & Evidence