Butyn-2-one → HCID 10911572, compound

HRID 1700512Notes

Reaction equation

HRID 1700512 reaction equation
[C:1]1([CH:7]2[CH2:12][C:11](=O)[CH2:10][C:9](=[O:14])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+:19].[CH3:20][C:21](=O)[C:22]#[CH:23]>C(O)C>[CH3:20][C:21]1[CH:22]=[CH:23][C:10]2[C:9](=[O:14])[CH2:8][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:12][C:11]=2[N:19]=1

Participants

5

Reactant 3

HCID 15018Butyn-2-oneHCID 517165Ammonium AcetateHCID 5689621,3-Cyclohexanedione, 5-phenyl-

Product 1

HCID 10911572HCID 10911572, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 5-phenylcyclohexane-1,3-dione (1.2 g) and ammonium acetate (0.49 g) in ethanol (30 ml) was added 3-butyn-2-one (0.44 g), and the mixture was stirred at room temperature for 1.5 hours and refluxed for 18 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethyl acetate. The solution was washed with sodium hydrogen carbonate solution, water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (EtOAc/hexane) to give colorless crystals of 2-methyl-7-phenyl-5,6,7,8-tetrahydroquinolin-5-one (0.88 g).

Workup

  1. temperaturerefluxed for 18 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with sodium hydrogen carbonate solution, water and saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-aa7361439da1477a8c03c53d1f0047bc
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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