Water → Benzofuran-6-carbaldehyde

HRID 408568

반응식

HRID 408568 반응식
[O:1]1[C:5]2[CH:6]=[C:7]([C:10](OC)=[O:11])[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1.C(Cl)Cl.O=[Mn]=O>[O:1]1[C:5]2[CH:6]=[C:7]([CH:10]=[O:11])[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1

참가 물질

8

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22481705Methyl 6-benzofurancarboxylate

생성물 1

HCID 14354086Benzofuran-6-carbaldehyde

시약·촉매·용매 3

HCID 14801Manganese dioxide촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a solution of methyl benzofuran-6-carboxylate (1 eq.) in dry THF was added a solution of LiAlH4 (1M in THF, 1.5 eq.) at 0° C. under argon. The reaction mixture was stirred at 0° C. for 2.5 h. Water, aqueous NaOH (2N) and water were then added and the mixture was stirred at 20° C. for 30 min. The crude was passed through a pad of celite and solvent removed under reduced pressure. To a solution of the residue (1 eq.) in DCM was added MnO2 (10 eq.). The dark suspension was stirred at 20° C. for 15 h, filtered through a pad of celite and the solvent removed under reduced pressure to afford benzofuran-6-carboxaldehyde which was used as such without further purification.

후처리

  1. stirringthe mixture was stirred at 20° C. for 30 min
  2. customremoved under reduced pressure
  3. stirringThe dark suspension was stirred at 20° C. for 15 h
  4. filtrationfiltered through a pad of celite
  5. customthe solvent removed under reduced pressure

출처 및 근거

ORD 기록
ord-3386ccb071944e28b405cbcb82431dfd
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759334B2

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