Quinoline → HCID 68473642, compound

HRID 1513519Notes

Reaction equation

HRID 1513519 reaction equation
N1C2C(=CC=CC=2)C=CC=1.[CH3:11][CH:12]1[CH2:26][CH2:25][O:24][C:23](=[O:27])[CH2:22][CH:21]=[CH:20][CH2:19][CH2:18][CH2:17][C:16]#[C:15][CH2:14][CH2:13]1>C(O)C.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[CH3:11][CH:12]1[CH2:26][CH2:25][O:24][C:23](=[O:27])[CH2:22][CH:21]=[CH:20][CH2:19][CH2:18][CH2:17][CH:16]=[CH:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 7047QuinolineHCID 86644216HCID 86644216, compound

Product 1

HCID 68473642HCID 68473642, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 702EthanolSolvent

Procedure

Quinoline (4.86 μL, 0.0411 mmol) and 10% Pd/BaSO4 (0.88 mg, 0.00824 mmol) were added to a stirred solution of (4E)-13-methyloxacyclopentadec-4-en-9-yn-2-one (48.2 mg, 0.206 mmol) in ethanol (2.0 mL). The reaction flask was flushed with argon followed by hydrogen, and the reaction mixture was stirred under hydrogen atmosphere at room temp. and ambient pressure. After 3.5 h, GC-monitoring indicated complete conversion, upon which the catalyst was filtered off through a pad of Celite and washed with ethanol. The solvent was removed under reduced pressure, and the resulting residue purified by chromatography on silica gel [20 g; pentane-Et2O (10:1); Rf=0.78 in pentane-Et2O (5:1)] to furnish (4E,9Z)-13-methyloxacyclopentadeca-4,9-dien-2-one (44.8 mg, 92%) as a colourless odoriferous liquid.

Workup

  1. customThe reaction flask was flushed with argon
  2. filtrationGC-monitoring indicated complete conversion, upon which the catalyst was filtered off through a pad of Celite
  3. washwashed with ethanol
  4. customThe solvent was removed under reduced pressure
  5. customthe resulting residue purified by chromatography on silica gel [20 g; pentane-Et2O (10:1); Rf=0.78 in pentane-Et2O (5:1)]

Sources & evidence

ORD record
ord-b1fe6f75e04f4f4795615f06f3a5ae86
Source dataset
uspto-grants-2012_07
Patent number
US08217185B2

Reaction notes

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