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Acetic Acid → (E)-2-Ethyl-3-[4-(3-pyridylmethyl)phenyl]acrylic acid ethyl ester

HRID 1680025
Notes
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Reaction equation

HRID 1680025 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([CH:8](P(=O)(OCC)OCC)[CH2:9][CH3:10])=[O:7])[CH3:4].COC(=O)/C=[CH:23]/[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)=[CH:26][CH:25]=1.C(O)(=O)C>O1CCCC1>[CH2:3]([O:5][C:6](=[O:7])/[C:8](/[CH2:9][CH3:10])=[CH:23]/[C:24]1[CH:25]=[CH:26][C:27]([CH2:30][C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)=[CH:28][CH:29]=1)[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 229053Ethyl 2-(diethoxyphosphoryl)butanoateHCID 12882181(E)-3-[4-(3-Pyridylmethyl)phenyl]acrylic acid methyl ester

Product 1

HCID 12904571(E)-2-Ethyl-3-[4-(3-pyridylmethyl)phenyl]acrylic acid ethyl esterYield 113.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 46 mg of sodium hydride(content 63%) in 3 ml of tetrahydrofuran was added dropwise 0.33 g of diethyl 1-ethoxycarbonylpropylphosphonate at room temperature, and the mixture was stirred at that temperature for 15 minutes. To it was added a solution of 206 mg of the aldehyde (prepared as described in Reference Example 1) in one ml, and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was acidified with acetic acid, and concentrated under reduced pressure. To the residue was added a saturated aqueous solution of sodium bicarbonate, and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (2:1) as eluent to give 273 mg of the title compound having the following physical characteristics:

Workup

  1. stirringthe mixture was stirred at room temperature for 1.5 hours
  2. concentrationconcentrated under reduced pressure
  3. additionTo the residue was added a saturated aqueous solution of sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel using
  9. additiona mixture of cyclohexane and ethyl acetate (2:1) as eluent

Sources & evidence

ORD record
ord-6be6ea5bfb0a46f980fd5853be9dfc56
Source dataset
uspto-grants-1981_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04271170

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes