Ethyl 5-methylhex-2-ynoate → (Z)-5-methyl-hex-2-enoic acid ethyl ester

HRID 1066908Notes

Reaction equation

HRID 1066908 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[C:5]#[C:6][CH2:7][CH:8]([CH3:10])[CH3:9])[CH3:2]>C1COCC1.N1C=CC=CC=1.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[CH2:1]([O:3][C:4](=[O:11])/[CH:5]=[CH:6]\[CH2:7][CH:8]([CH3:10])[CH3:9])[CH3:2]

Participants

5

Reactant 1

HCID 12383857Ethyl 5-methylhex-2-ynoate

Product 1

HCID 10241046(Z)-5-methyl-hex-2-enoic acid ethyl esterYield 56.5%

Reagents, catalysts & solvents 3

HCID 16218511Pd barium sulfateCatalystHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Methyl-hex-2-ynoic acid ethyl ester 7 (20.97 g) in THF (540 mL), pyridine (60 mL), and 5% Pd/BaSO4 (1.10 g) was hydrogenated in 3.25 hours. The solvent was evaporated, and the light oil was chromatographed on a silica gel coulmn. After recovering some unreacted acetylene, the olefin was eluted with 5% ether in pet ether to give pure fractions of (Z)-5-methyl-hex-2-enoic acid ethyl ester 8 (12.0 g).

Workup

  1. customThe solvent was evaporated
  2. customthe light oil was chromatographed on a silica gel coulmn
  3. customAfter recovering some unreacted acetylene
  4. washthe olefin was eluted with 5% ether in pet ether

Sources & evidence

ORD record
ord-da3213aa623c4ae18f56183480a5d8a3
Source dataset
uspto-grants-2001_06
Patent number
US06245801B1

Reaction notes

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