Hydrochloric Acid → methyl (E)-3-[5-(4-methylphenyl)furan-2-yl]acrylate

HRID 2228210Notes

Reaction equation

HRID 2228210 reaction equation
CN(OC)[C:3]([C:5]1[O:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)=O.[H-].C([Al+]CC(C)C)C(C)C.Cl.[OH2:30].[O:31]1[CH2:35]C[CH2:33][CH2:32]1>C1(C)C=CC=CC=1>[CH3:16][C:13]1[CH:12]=[CH:11][C:10]([C:7]2[O:6][C:5](/[CH:3]=[CH:33]/[C:32]([O:31][CH3:35])=[O:30])=[CH:9][CH:8]=2)=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 18472441HCID 18472441, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 86756170methyl (E)-3-[5-(4-methylphenyl)furan-2-yl]acrylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

Under nitrogen atmosphere, to a solution of N-methyl-N-methoxy-5—(4-methylphenyl)furan-2-carboxamide (2.5 g) in tetrahydrofuran (20 ml) was added diisobutylaluminum hydride (1.01M toluene solution) (15 ml) at −78° C., and the mixture was stirred at −78° C. for 10 minutes and then at 0° C. for 15 minutes. To the reaction mixture was added 1N hydrochloric acid to stop the reaction, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1:5→1:4) to give crude product (1.49 g). A solution of the crude aldehyde (1.49 g) and methyl (triphenylphosphoranilidene)acetate (2.67 g) in toluene (30 ml) was refluxed under nitrogen atmosphere for 1 hour and cooled. To the mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride. solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1:9→1:5) to give methyl (E)-3-[5—(4-methylphenyl)furan-2-yl]acrylate (1.63 g) as pale yellow crystals.

Workup

  1. waitat 0° C. for 15 minutes
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was separated
  8. custompurified with column chromatography (ethyl acetate/hexane=1:5→1:4)
  9. customto give crude product (1.49 g)
  10. temperaturecooled
  11. extractionthe mixture was extracted with ethyl acetate
  12. washThe organic layer was washed with saturated sodium chloride
  13. dry with materialsolution, dried with magnesium sulfate
  14. concentrationconcentrated under reduced pressure
  15. customThe residue was separated
  16. custompurified with column chromatography (ethyl acetate/hexane=1:9→1:5)

Sources & evidence

ORD record
ord-1a75c61f248649b3be16b1b476aee4aa
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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