Triethyl phosphonoacetate → Ethyl 3-(2,3,4-trimethoxyphenyl)prop-2-enoate

HRID 1267625Notes

Reaction equation

HRID 1267625 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH3:17][O:18][C:19]1[C:26]([O:27][CH3:28])=[C:25]([O:29][CH3:30])[CH:24]=[CH:23][C:20]=1[CH:21]=O>C1COCC1>[CH3:17][O:18][C:19]1[C:26]([O:27][CH3:28])=[C:25]([O:29][CH3:30])[CH:24]=[CH:23][C:20]=1[CH:21]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 750062,3,4-Trimethoxybenzaldehyde

Product 1

HCID 67200008Ethyl 3-(2,3,4-trimethoxyphenyl)prop-2-enoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil; 245 mg) was suspended in THF (1 mL) under an argon atmosphere, to the suspension ethyl diethylphosphonoacetate (1.11 mL) was added dropwise under ice cooling, and the mixture was stirred for 30 minutes. After 2,3,4-trimethoxybenzaldehyde (1.0 g) was then added to the mixture, the reaction mixture was stirred at room temperature for 30 minutes and concentrated under reduced pressure. The residue was dissolved in chloroform, and the solution was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to obtain the title compound.

Workup

  1. additionwas added dropwise under ice cooling
  2. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform
  5. washthe solution was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-ad0405e069a04048add29f64914eab36
Source dataset
uspto-grants-2003_04
Patent number
US06552188B2

Reaction notes

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