Water → methyl (E,E)-4-ethyl-2,4-heptadienoate

HRID 2295014Notes

Reaction equation

HRID 2295014 reaction equation
C[O-].[Na+].[CH2:4]([O:6][C:7](=[O:17])[C:8](CC)(CC)P(O)(O)=O)C.[CH2:18](/[C:20](=[CH:23]\[CH2:24][CH3:25])/[CH:21]=O)[CH3:19].O>CO>[CH2:18](/[C:20](=[CH:23]\[CH2:24][CH3:25])/[CH:21]=[CH:8]/[C:7]([O:6][CH3:4])=[O:17])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 53644392-Pentenal, 2-ethyl-HCID 10942334Sodium MethoxideHCID 17846631Ethyl diethyl-phosphonoacetate

Product 1

HCID 12700325methyl (E,E)-4-ethyl-2,4-heptadienoateYield 77.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 28 wt % solution of sodium methoxide in methanol (25.7 g) at 10° C. were added dropwise diethyl phosphonoacetic acid ethyl ester (25.3 g) and (E)-2-ethyl-2-pentenal (11.5 g) successively under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 3 hours, poured into chilled water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (dichloromethane) to give 13.4 g of methyl (E,E)-4-ethyl-2,4-heptadienoate as an oil.

Workup

  1. additionpoured
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel (dichloromethane)

Sources & evidence

ORD record
ord-42ceaf244aec4e628be00ff2ba7ddf13
Source dataset
uspto-grants-1997_11
Patent number
US05691366

Reaction notes

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