Triethylamine → HCID 12973079, compound

Participants

Reaction Steps

To a cooled (0° C.) solution of 3-(3-pyridyl)-1-(5,6,7,8-tetrahydronaphthalen-2-yl)propanol (2.29 g) in CH2Cl2 (50 ml) were added triethylamine (2.4 ml) and methanesulfonyl chloride (0.86 ml ). The mixture was stirred at room temperature for 16 hours. The mixture was washed with water and brine, dried and concentrated. The residue was mixed with 1,8-diazabicyclo[5.4.0]undec-7-ene (2.59 g) and stirred at 100° C. for 45 minutes. 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)-(5,6,7,8-tetrahydronaphthalen-2-yl)-2-propen-1-yl]pyridine (216 mg) and 3-[(Z)-(5,6,7,8-tetrahydronaphthalen-2-yl)-2-propen-1-yl]pyridine (245 mg). 3-[(E)-(5,6,7,8-Tetrahydronaphthalen-2-yl)-2-propen-1-yl]pyridine

Provenance & Evidence