Pyridine → 3-Octen-1-ol, (3Z)-

HRID 1065949Notes

Reaction equation

HRID 1065949 reaction equation
[H][H].[CH2:3]([OH:11])[CH2:4][C:5]#[C:6][CH2:7][CH2:8][CH2:9][CH3:10].N1C=CC=CC=1>CCCCCC.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[CH2:3]([OH:11])[CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 3

HCID 1049PyridineHCID 846943-Octyn-1-olHCID 178418361HCID 178418361, compound2×

Product 1

HCID 53645193-Octen-1-ol, (3Z)-

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8058HexaneSolvent

Procedure

Hydrogen gas was blown into a solution prepared by dissolving 126 g of 3-octyn-1-ol in 100 ml of n-hexane with admixture of 10 g of a Lindlar catalyst and 10 g of pyridine and the introduction of hydrogen was continued for about 4 hours when absorption of hydrogen had ceased. Removal of solid matter from the reaction mixture by filtration and stripping of n-hexane gave cis-3-octen-1-ol, which was dissolved in a mixture of 250 g of methylene chloride and 111 g of triethylamine.

Workup

  1. customprepared
  2. customwhen absorption of hydrogen
  3. customRemoval of solid matter from the reaction mixture
  4. filtrationby filtration and stripping of n-hexane

Sources & evidence

ORD record
ord-5801914454af4891bf2b6430f9e7ec1e
Source dataset
uspto-grants-1982_05
Patent number
US04331820

Reaction notes

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