Tetrahydrofuran → (E)-3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)acrylic acid ethyl ester

HRID 2247481Notes

Reaction equation

HRID 2247481 reaction equation
C1COCC1.[H-].[Na+].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[N:18]1[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]1)[CH:13]=O.[C:24]([O:27][CH2:28][CH3:29])(=[O:26])[CH3:25]>O>[CH2:28]([O:27][C:24](=[O:26])/[CH:25]=[CH:13]/[C:12]1[CH:15]=[CH:16][C:17]([N:18]2[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]2)=[C:10]([O:9][CH3:8])[CH:11]=1)[CH3:29]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

Product 1

HCID 66961330(E)-3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)acrylic acid ethyl esterYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a THF (15 mL) solution of sodium hydride (814 mg) triethylphosphonoacetic acid (4.1 mL) was added at 0° C., and the reaction solution was agitated at 0° C. for 30 minutes and at room temperature for 1 hour. After cooling the reaction solution at 0° C., the THF (5 mL) solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (4.0 g) synthesized in Example 1 was added dropwise to the reaction solution. The reaction solution was further agitated at 0° C. for 30 minutes and then at room temperature for 2 hours. Ethyl acetate and water was added to the reaction solution, and the organic layer was separated and washed with a saturated ammonium chloride solution. After drying with anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. By re-crystallizing the obtained solid using a mixed solution of hexane and ethyl acetate, the 4.55 g (86%) title compound was obtained. The physical properties of the compound are as follows.

Workup

  1. temperatureAfter cooling the reaction solution at 0° C.
  2. stirringThe reaction solution was further agitated at 0° C. for 30 minutes
  3. waitat room temperature for 2 hours
  4. customthe organic layer was separated
  5. washwashed with a saturated ammonium chloride solution
  6. dry with materialAfter drying with anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customBy re-crystallizing the obtained solid

Sources & evidence

ORD record
ord-ac7b89ac422247f29fdca24f42b1fc75
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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