Phosphorus oxide (P4O10) → Ethyl [2-methyl-4-({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}acetyl)phenoxy]acetate

Participants

Reaction Conditions

Reaction Steps

A well stirred suspension of phosphorus pentoxide (0.92 g) in methane sulfonic acid (6.5 ml) under nitrogen was heated to 60° C. until a clear solution formed. The mixture was then allowed to cool to room temperature prior to addition of {4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}acetic acid (intermediate 14, 0.98 g) and ethyl (2-methylphenoxy)acetate (0.49 ml). The mixture was heated to 60° C. for 90 minutes, after cooling to room temperature the reaction mixture was poured onto iced water (100 ml) and the acidic suspension basified by cautious addition of solid sodium bicarbonate. The product was extracted into ethyl acetate and the combined organic extracts dried (magnesium sulfate) filtered and evaporated. Purification by flash column chromatography using ethyl acetate:cyclohexane (1:9) as eluent gave title compound as a pale yellow solid.

Provenance & Evidence