Ethyl Acetate → 1-[2-(3-Chloro-phenyl)-2H-tetrazol-5-yl]-ethanone

Participants

Reaction Steps

The title compound of Example 10.1 (1.50 g, 5.06 mmol) was dissolved in dichloromethane (79 mL) and ozone was bubbled through the solution for a period of 15 minutes. The solution turned from orange to a darker orange colour. The reaction completeness was checked using a 10% EtOAc:hexanes TLC solvent system. Oxygen was bubbled through the solution for an additional 5 minutes to remove any excess ozone remaining. Dimethyl sulfide (5 mL) was added to the solution and the mixture was allowed to equilibrate to room temperature. The solvent was removed under vacuum and an oily brown substance remained. A 3 cm flash column was prepared containing 15 cm silica and ˜3 cm sand. The column was run using a 5% EtOAc:hexanes solvent system. The eluted fractions containing the product were collected and concentrated under low pressure. Flash column chromatography (silica, 5% EtOAc:hexanes) yielded 893 mg (79.4% yield) of the title compound.

Provenance & Evidence