Quinoline → (3Z,9Z)-2,7-dimethyltrideca-3,9-diene-2,5-diol

HRID 2059554Notes

Reaction equation

HRID 2059554 reaction equation
N1C2C(=CC=CC=2)C=CC=1.[CH3:11][C:12]([OH:27])([C:14]#[C:15][CH:16]([OH:26])[CH2:17][CH:18]([CH3:25])[CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH3:24])[CH3:13]>C(O)C.[Pd]>[CH3:11][C:12]([OH:27])(/[CH:14]=[CH:15]\[CH:16]([OH:26])[CH2:17][CH:18]([CH3:25])[CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH3:24])[CH3:13]

Participants

5

Reactant 2

HCID 7047QuinolineHCID 86625208(9Z)-2,7-dimethyltridec-9-en-3-yne-2,5-diol

Product 1

HCID 86625209(3Z,9Z)-2,7-dimethyltrideca-3,9-diene-2,5-diolYield 55.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

At room temp., 520 mg (0.488 mmol) of 10% palladium on barium sulphate and 190 mg (1.47 mmol) of quinoline were added to a stirred solution of 7.70 g (32.3 mmol) of this (9Z)-2,7-dimethyltridec-9-en-3-yne-2,5-diol in 170 mL of ethanol. The flask was evacuated and flushed with nitrogen three times, and three times evacuated and flushed with hydrogen. The resulting reaction mixture was then stirred for 1.5 h under an atmosphere of hydrogen at ambient pressure and temperature, prior to evacuation and ventilation with nitrogen. The reaction flask was opened to air, and the catalyst filtered off by suction over a pad of Celite. After removal of the solvent in a rotary evaporator under reduced pressure, the resulting crude product (8.07 g) was purified by flash chromatography (100 g of silica gel, pentane/ether, 1:1, Rf=0.28) to afford 4.28 g (55%) of (3Z,9Z)-2,7-dimethyltrideca-3,9-diene-2,5-diol as a colorless oil.

Workup

  1. customThe flask was evacuated
  2. customflushed with nitrogen three times, and three times
  3. customevacuated
  4. customflushed with hydrogen
  5. customThe resulting reaction mixture
  6. filtrationthe catalyst filtered off by suction over a pad of Celite
  7. customAfter removal of the solvent
  8. customin a rotary evaporator under reduced pressure
  9. customthe resulting crude product (8.07 g) was purified by flash chromatography (100 g of silica gel, pentane/ether, 1:1, Rf=0.28)

Sources & evidence

ORD record
ord-f0c7fd6f53dd429eacba6619bfac7fb3
Source dataset
uspto-grants-2012_10
Patent number
US08278230B2

Reaction notes

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