Dimethylformamide → HCID 19363280, compound

Participants

Reaction Steps

2-(4-Methoxy-3-pentyloxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole (500 mg, 1.76 mmol) and DMF (8 ml) were mixed, and this solution was cooled to -60° C. n-Butyllithium (1.6M hexane solution, 2.42 ml, 3.87 mmol) was added and the mixture was stirred for 1 hour. Dimethyl disulfide (0.35 ml, 3.87 mmol) was added to this solution, and the mitxure was stirred at room temperature for 1 hour. Water (5 ml) was added, and the aqueous layer was extracted 3 times with ethyl acetate (10 ml). The organic layers were combined and concentrated under reduced pressure. A 3N hydrochloric acid (4 ml) was added to the obtained residue and the mixture was under heating for 3 hours. A 10N aqueous sodium hydroxide solution (4 ml) was added and the mixture was refluxed under heating for 2 hours. A concentrated hydrochloric acid (3 ml) was added to make the reaction mixture acidic, and the aqueous layer was extracted 4 times with ethyl acetate (20 ml). The organic layers were combined, washed 3 times with saturated brine (10 ml) and dried over anhydrous magnesium sulfate. The drying agent was filtered off and the filtrate was concentrated under reduced pressure. The obtained crude crystals were purified by washing with hexane to give 4-methoxy-2-methylthio-3-pentyloxybenzoic acid (370 mg, 74%) as pale-brown crystals.

Provenance & Evidence