Quinoline → HCID 68479074, compound

HRID 1513522Notes

Reaction equation

HRID 1513522 reaction equation
N1C2C(=CC=CC=2)C=CC=1.[CH3:11][CH:12]1[CH2:25][CH2:24][O:23][C:22](=[O:26])[CH2:21][CH:20]=[CH: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[CH2:25][CH2:24][O:23][C:22](=[O:26])[CH2:21][CH:20]=[CH:19][CH2:18][CH2:17][CH:16]=[CH:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 7047QuinolineHCID 86644220HCID 86644220, compound

Product 1

HCID 68479074HCID 68479074, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 702EthanolSolvent

Procedure

Quinoline (27.5 μL, 0.232 mmol) and 10% Pd/BaSO4 (4.90 mg, 0.0461 mmol) were added to a stirred solution of (4E)-12-methyloxacyclotetradec-4-en-8-yn-2-one (256 mg, 1.16 mmol) in ethanol (20 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 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 [30 g; pentane-Et2O (20:1); Rf=0.60 in pentane-Et2O (5:1)] to furnish (4E,8Z)-12-methyloxacyclotetradeca-4,8-dien-2-one (223 mg, 86%) 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 [30 g; pentane-Et2O (20:1); Rf=0.60 in pentane-Et2O (5:1)]

Sources & evidence

ORD record
ord-3f6e7fda11dc4a9d9999d6e433747349
Source dataset
uspto-grants-2012_07
Patent number
US08217185B2

Reaction notes

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