Ethyl Acetate → HCID 19081691, compound

HRID 963406Notes

Reaction equation

HRID 963406 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:23])[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:8][N:9]2[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[C:24](C1(C)C(O)=C(C(C)(C)C)C=C(C)C1)(C)(C)[CH3:25].C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][CH:3]=[C:2]([CH:24]=[CH2:25])[CH:11]=3)[C:6](=[O:23])[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:8]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 19081700HCID 19081700, compoundHCID 67047598HCID 67047598, compound

Product 1

HCID 19081691HCID 19081691, compoundYield 9,385.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1 g of ethyl 7-bromo-1-cyclohexyl-4-oxo-1,4-dihydro-quinoline-3-carboxylate (Example 13ad)), 60 mg of palladium tetrakis-triphenylphosphine, 1.55 ml of tributyl-vinyl-stannate and 5 mg of 2,6-di-tert-butyl-4-methyl-cresol in 25 ml of toluene is heated at reflux for 1 hr. The reaction mixture is cooled to room temperature, treated with 100 ml of ethyl acetate and washed with 100 ml of 10% aqueous ammonia solution. The aqueous solution is extracted with 50 ml of ethyl acetate. The combined organic phases are washed with 100 ml of saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated. The residue is chromatographed on silica gel with hexane/ethyl acetate 1:1. 0.646 g (75%) of ethyl 1-cyclohexyl-4-oxo-7-vinyl-1,4-dihydro-quinoline-3-carboxylate is obtained as a colourless amorphous solid. Mass spectrum (ISP): 326.3(M++H, 100%).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 hr
  3. washwashed with 100 ml of 10% aqueous ammonia solution
  4. extractionThe aqueous solution is extracted with 50 ml of ethyl acetate
  5. washThe combined organic phases are washed with 100 ml of saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated
  8. customThe residue is chromatographed on silica gel with hexane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-112c28fdb349418388743332914160f7
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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