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

HRID 1277194ノート

反応式

HRID 1277194 の反応式
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-].Cl.[OH2:21]>O1CCCC1.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:3]/[C:5]([O:6][CH3:7])=[O:21])=[CH:9][CH:8]=2)=[CH:15][CH:14]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 166653HydrideHCID 18472441HCID 18472441、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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 duisobutylaluminum 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.

後処理

  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)

出典と根拠

ORDレコード
ord-3c17b388942040cd940bd71bd6d34163
出典データセット
uspto-grants-2000_12
特許番号
US06166006

反応ノート

読み込み中…