Triethylamine → HCID 11200112, compound

Participants

Reaction Steps

The tert-butyl 4-(3-hydroxyphenyl)-3,6-dihydropyridine-1(2H)-carboxylate (4.01 g, 14.58 mmol), tert-butyldimethylsilyl chloride (2.73 g, 18.22 mmol), triethylamine (4.01 g, 40.0 mmol) and a catalytic amount of dimethylaminopyridine (100 mg, 0.80 mmol) were mixed in dichloromethane (100 mL) at room temperature for 16 h. The solvent was removed at reduced pressure and the resulting semisolid dissolved in diethylether (100 mL). The solution was extracted with 1N aqueous hydrochloric acid (2×50 mL), extracted with saturated aqueous sodium bicarbonate (2×50 mL), and extracted with saturated with saturated aqueous ammonium chloride (2×50 mL). The solution was dried over sodium sulfate and solvent removed at reduced pressure. The tert-butyl 4-(3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3,6-dihydropyridine-1(2H)-carboxylate (4.8 g, 12.33 mmol) was isolated as a clear colorless oil by preparative silica chromatography (5% ethyl acetate/95% hexanes). HRMS m/z 388.2305 (calcd for M−H 388.2302.)

Provenance & Evidence