Water → HCID 14796234, compound

Participants

Reaction Steps

To a solution of 2,6-di-tert-butyl-4-mercaptophenol (II) (590 mg; 2.48 mmol) in dry ether (10 ml), triethylamine (303 mg; 3 mmol) was added, and a solution of ethyl 4-bromocrotonate (580 mg; 3 mmol) in dry ether (5 ml) was added while cooling with ice, followed by stirring at room temperature for 2 hours. The reaction mixture was combined with water (50 ml) and extracted with ether (50 ml). The extract was washed with water (50 ml) two times and concentrated under reduced pressure. The crude intermediate product as pale yellow oil was dissolved in ethanol (30 ml), 10 % sodium hydroxide solution (3 ml) was added thereto, and the resultant mixture was stirred at room temperature for 2 hours. To the reaction mixture, acetic acid (2 ml) was added, and the resulting mixture was concentrated under reduced pressure to make a volume of about 10 ml, which was extracted with ethyl acetate (50 ml). The extract was washed with water (50 ml) two times, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residual oil was chromatographed on silica gel and eluted with ethyl acetate. The collected fractions were concentrated under reduced pressure, and the crystalline residue was recrystallized from n-pentane to give the objective compound (Ih) (270 mg). m.p., 104°-106° C. Yield, 34 %.

Provenance & Evidence