Aluminum(III) Chloride → 3-(4-Hydroxy-3,5-di-methoxy-benzoyl)-7-hydroxy-6-methoxy-2-Methyl-benzo[b]furan

HRID 1020505Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1020505
[CH3:1][C:2]1[O:6][C:5]2[C:7]([OH:13])=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:4]=2[C:3]=1[C:14](=[O:27])[C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23]C)=[C:17]([O:25][CH3:26])[CH:16]=1.[Cl-].[Cl-].[Cl-].[Al+3]>ClCCl>[OH:23][C:18]1[C:19]([O:21][CH3:22])=[CH:20][C:15]([C:14]([C:3]2[C:4]3[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([OH:13])[C:5]=3[O:6][C:2]=2[CH3:1])=[O:27])=[CH:16][C:17]=1[O:25][CH3:26]

Komponenten

4

Edukt 2

HCID 6451240Aluminum(III) Chloride2×HCID 24786555Bnc-105

Produkt 1

HCID 248803213-(4-Hydroxy-3,5-di-methoxy-benzoyl)-7-hydroxy-6-methoxy-2-Methyl-benzo[b]furan

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Methyl-3-(3,4,5-trimethoxybenzoyl)-7-hydroxy-6-methoxy-benzo[b]furan Example 11 (100 mg, 0.27 mmol) was dissolved in dry dichloromethane (5 mL) and solid aluminium trichloride (72 mg, 0.54 mmol) was added to it. The mixture was stirred for 2 hours when additional amount of aluminium trichloride (72 mg, 0.54 mmol) was added and the stirring was continued for 2 more hours (tlc). The reaction was quenched with saturated solution of ammonium chloride and diluted with DCM (20 mL) the organic layer was separated and washed with water, dried over magnesium sulphate and solvent was distilled to gave the crude product which was purified over silica gel column. The compound was crystallized from methanol to gave the product as white solid. (42 mg, 44%). 1H NMR (300 MHz, CDCl3) δ 7.16 (s, 2H, benzoyl Hs), 6.91 (d, J=8.58 Hz, 1H), 6.83 (d, J=8.58 Hz, 1H), 5.94 (s, 1H, OH), 5.68 (s, 1H, OH), 3.91 (s, 3H, OMe), 3.87 (s, 6H, 2×OMe), 2.54 (s, 3H, Me).

Aufarbeitung

  1. additionwas added
  2. customThe reaction was quenched with saturated solution of ammonium chloride
  3. additiondiluted with DCM (20 mL) the organic layer
  4. customwas separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate and solvent
  7. distillationwas distilled
  8. customto gave the crude product which
  9. customwas purified over silica gel column
  10. customThe compound was crystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-6fe0b8687c75441b95c7dc4cf444d353
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716335B2

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