Triethylamine → HCID 14884153, compound

Participants

Reaction Steps

To 1.4 g (10.5 millimoles) of 1,2,3,4-tetrahydroquinoline were added 1.2 g (11.9 millimoles) of triethylamine and 10 ml of toluene, and a solution of 1.5 g (11.5 millimoles) of 2-furoyl chloride in 10 ml of toluene was added dropwise to the mixture at room temperature. The mixture was stirred for 1 hour and water and ethyl acetate were added to the mixture, and the organic layer was separated, dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure to obtain a brown solid. The solid was dissolved in 20 ml of THF and the solution was added dropwise to a suspension of 0.5 g (13.2 millimoles) of lithium aluminum hydride in 20 ml of THF at room temperature. The mixture was heated and refluxed for 1 hour, and 1 ml of water and ether were added to the mixture. Then, anhydrous magnesium sulfate was added to the mixture, and the mixture was stirred for 30 minutes. The solid was removed by filtration, and the obtained filtrate was concentrated to dryness under reduced pressure to obtain a light-yellow liquid. The obtained liquid was purified by the silica gel column chromatography (developing solvent: ethyl acetate/hexane=1/15) to obtain 0.5 g (the yield was 23%) of intended compound No. 2 in the form of a light-yellow liquid.

Provenance & Evidence