N-methoxy-N,3-dimethylthiophene-2-carboxamide → (4-Ethylphenyl)(3-methylthiophen-2-yl)methanone

Participants

Reaction Steps

To a solution of N-methoxy-N,3-dimethylthiophene-2-carboxamide (52) (J. Med. Chem., 2001, 44, 863) (5.00 g, 27.0 mmole) in THF (30 mL) was added 4-ethylphenylmagnesium bromide (0.5M in THF, 108 mL, 54.0 mmole) at 0° C. The resulting solution was stirred at ambient temperature overnight. The reaction mixture was quenched by adding MeOH (20 mL) and concentrated in vacuo. The crude residue was purified on Biotage® purification apparatus to yield the compound 53 (4-ethylphenyl)(3-methylthiophen-2-yl)methanone (4.42 g, 19.2 mmole, 71%) as brown oil.

Provenance & Evidence