Ethyl 2-methyl-3,4-pentadienoate → ethyl (2E)-2-methylpenta-2,4-dienoate

HRID 1749117Notes

Reaction equation

HRID 1749117 reaction equation
[O-]CC.[Na+].[CH3:5][CH:6]([CH:12]=[C:13]=[CH2:14])[C:7]([O:9][CH2:10][CH3:11])=[O:8]>C(O)C>[CH3:5]/[C:6](=[CH:12]\[CH:13]=[CH2:14])/[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 62166Ethyl 2-methyl-3,4-pentadienoateHCID 2723922Sodium ethoxide

Product 1

HCID 6372304ethyl (2E)-2-methylpenta-2,4-dienoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethoxide solution (21% in ethanol, 33.3 ml, cat.) was added to a solution of ethyl 2-methylpenta-3,4-dienoate (Bedoukian, 125.0 g, 890 mmol) in anhydrous ethanol (350 ml) and stirred at ambient temperature for 12 hours. The solution was concentrated in vacuo and the residue partitioned between ether and saturated NH4Cl solution. The aqueous phase was re-extracted twice with ether, then the combined organic phase washed with NH4Cl and then brine, dried over Na2SO4, filtered and the solvents removed in vacuo to yield the crude ester, 125.8 g as an orange oil which was used directly in the next step without further purification.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue partitioned between ether and saturated NH4Cl solution
  3. extractionThe aqueous phase was re-extracted twice with ether
  4. washthe combined organic phase washed with NH4Cl
  5. dry with materialbrine, dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-327c38d476ca44b78c732aec9b390698
Source dataset
uspto-grants-2015_10
Patent number
US09156770B2

Reaction notes

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