Quinoline → 2,5-Undecadien-1-ol, (2Z,5Z)-

HRID 615555Notes

Reaction equation

HRID 615555 reaction equation
[CH2:1]([OH:12])[C:2]#[C:3][CH2:4][C:5]#[C:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].N1C2C(=CC=CC=2)C=CC=1.[H][H]>C(O)C.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[CH2:1]([OH:12])/[CH:2]=[CH:3]\[CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 7047QuinolineHCID 111163932,5-undecadiyn-1-olHCID 178418361HCID 178418361, compound

Product 1

HCID 117450382,5-Undecadien-1-ol, (2Z,5Z)-Yield 69.6%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

2,5-undecadiyn-1-ol (1.5 g) in absolute ethanol (15 ml) was reduced with Lindlar catalyst (0.33 g) in the presence of quinoline (0.1 ml) at 25° C., 1 atm., for 7 h. The uptake of hydrogen stopped at 420 ml (theoretical 428 ml). The solution was filtered, and the solvent was evaporated to give 1.5 g of crude product which was then purified by column chromatography on silica gel (50 g). Elution with ether-petroleum ether (1:4 parts by volume) gave 1.07 g of (Z,Z)-2,5-undecadien-1-ol as an oil.

Workup

  1. filtrationThe solution was filtered
  2. customthe solvent was evaporated
  3. customto give 1.5 g of crude product which
  4. customwas then purified by column chromatography on silica gel (50 g)
  5. washElution with ether-petroleum ether (1:4 parts by volume)

Sources & evidence

ORD record
ord-d89afb0e710344bd8c25c282fef498c8
Source dataset
uspto-grants-1985_02
Patent number
US04500462

Reaction notes

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