Hydrochloric Acid → HCID 67812940, compound

Participants

Reaction Steps

To a cooled (−40° C.) solution of N-methoxy-N,4,5-trimethylthiophene-3-carboxamide (1.77 g, 8.88 mmol) in THF (10 mL) was slowly added (over 10 min) a solution of 4-chlorophenylmagnesium bromide (17 mL, 17.00 mmol, 1 M) in diethyl ether. The reaction mixture was allowed to gradually warm to room temperature and age for several hours. To the mixture was added 1 N HCl and the aqueous layer was extracted with EtOAc (2×). The combined organic layer was washed with saturated NaHCO3, water, dried over Na2SO4, and concentrated to give an oil. The resultant oil was purified on Biotage system (gradient elution 1% EtOAc:99% Hexanes to 4% EtOAc:96% Hexanes) to give the titled compound as white solids (2.00 g, 7.96 mmol, 90% yield). LC/MS m/z 251 [M+H]+.

Provenance & Evidence