Triethylamine → HCID 12973078, compound

Participants

Reaction Steps

To a cooled (0° C.) solution of 1-(2-naphthyl)-3-(3-pyridyl)propan-1-ol (1.14 g) in CH2Cl2 (30 ml) were added triethylamine (2.5 ml), methanesulfonyl chloride (0.70 ml) and catalytic amount of 4-methylaminopyridine. The mixture was stirred at room temperature for 8 hours. The mixture was washed with water and brine, dried and concentrated. The residue was dissolved in 1,8-diazabicyclo[5.4.0]undec-7-ene (20 ml) and stirred at 90° C. for 1 hour. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried and concentrated. The residue was chromatographed on silica gel (hexane-ethyl acetate=3:1) to give 3-[(E)-3-(2-naphthyl)-2-propen-1-yl]pyridine (123 mg) and 3-[(Z)-3-(2-naphthyl)-2-propen-1-yl]pyridine (67 mg). 3-[(E)-3-(2-naphthyl)-2-propen-1-yl]pyridine.

Provenance & Evidence