Piperonal → Ethyl 5-(2H-1,3-benzodioxol-5-yl)penta-2,4-dienoate

HRID 652958Notes

Reaction equation

HRID 652958 reaction equation
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6](/[CH:8]=[CH:9]/[CH2:10]P(OCC)(OCC)=O)=[O:7].[CH:19]1[C:24]([CH:25]=O)=[CH:23][C:22]2[O:27][CH2:28][O:29][C:21]=2[CH:20]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:28]1[O:29][C:21]2[CH:20]=[CH:19][C:24]([CH:25]=[CH:10][CH:9]=[CH:8][C:6]([O:5][CH2:4][CH3:3])=[O:7])=[CH:23][C:22]=2[O:27]1

Participants

6

Reactant 4

HCID 8438PiperonalHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomers

Product 1

HCID 54007855Ethyl 5-(2H-1,3-benzodioxol-5-yl)penta-2,4-dienoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.85 g (46.3 mmol) of a mineral oil containing 60% sodium hydride in dry tetrahydrofuran (100 ml) was added in an argon atmosphere 10.6 ml (47.8 mmol) of triethyl 4-phosphonocrotonate. The mixture was reacted at 0° C. for 1 hour, followed by addition of 4.86 g (32.3 mmol) of piperonal. The mixture was reacted at room temperature for 1.5 hours. Saturated aqueous solution of ammonium chloride was added to the reaction solution, and the resulting mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure and subjected to silica gel column chromatography. There was obtained 7.23 g (29.6 mmol) of ethyl 5-(3,4-methylenedioxyphenyl)-2,4-pentadienoate. Spectrophotometric data of the product support the structure shown below. ##STR73##

Workup

  1. customThe mixture was reacted at 0° C. for 1 hour
  2. customThe mixture was reacted at room temperature for 1.5 hours
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-97d1ff8c2df84d1baa843f22e833bd68
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

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