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

HRID 1387949Notes

Reaction equation

HRID 1387949 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 diisobutyl-aluminum 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 solution
  13. dry with materialdried 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-19e39baf09cd48debb8af6372b375381
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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