Triethylamine → HCID 14884153, compound

HRID 1088435Notes

Reaction equation

HRID 1088435 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23](Cl)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1.C1COCC1.CCOCC.O.C(OCC)(=O)C>[N:1]1([CH2:23][C:19]2[O:18][CH:22]=[CH:21][CH:20]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

11

Reactant 5

HCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 682422-Furancarbonyl chlorideHCID 694601,2,3,4-TetrahydroquinolineHCID 21226445Aluminium lithium hydride

Product 1

HCID 14884153HCID 14884153, compoundYield 23%

Reagents, catalysts & solvents 5

HCID 962WaterSolvent2×HCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried with anhydrous sodium sulfate
  3. concentrationconcentrated to dryness under reduced pressure
  4. customto obtain a brown solid
  5. temperatureThe mixture was heated
  6. temperaturerefluxed for 1 hour
  7. stirringthe mixture was stirred for 30 minutes
  8. customThe solid was removed by filtration
  9. concentrationthe obtained filtrate was concentrated to dryness under reduced pressure
  10. customto obtain a light-yellow liquid
  11. customThe obtained liquid was purified by the silica gel column chromatography (developing solvent: ethyl acetate/hexane=1/15)
  12. customto obtain 0.5 g (the yield was 23%) of intended compound No

Sources & evidence

ORD record
ord-d133226b982845318ea42953dd787701
Source dataset
uspto-grants-1990_10
Patent number
US04962200

Reaction notes

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