Ethanol → 2-Acetyl-7-(3,5-diisopropyl-2-propoxyphenyl)-benzo[b]furan

HRID 1394585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1394585
[CH:1]([C:4]1[C:5]([O:16][CH2:17][CH2:18][CH3:19])=[C:6](B(O)O)[CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)([CH3:3])[CH3:2].[C:20](=[O:23])([O-])[O-].[Na+].[Na+].O.[CH2:27]([OH:29])[CH3:28]>C1(C)C=CC=CC=1>[C:27]([C:20]1[O:23][C:2]2[C:1]([C:4]3[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[C:6]([CH:6]([CH3:7])[CH3:5])[C:5]=3[O:16][CH2:17][CH2:18][CH3:19])=[CH:3][CH:9]=[CH:4][C:1]=2[CH:2]=1)(=[O:29])[CH3:28]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 962WaterHCID 10340Sodium CarbonateHCID 121440122-Propoxy-3,5-diisopropyl-phenylboronic acid

Produkt 1

HCID 179527302-Acetyl-7-(3,5-diisopropyl-2-propoxyphenyl)-benzo[b]furan

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 1.08 mmol of (3,5-diisopropyl-2-propoxy-phenyl)-boronic acid, 498 mg (1.62 mmol) of 2-acetyl-7-trifluoromethanesulfonate benzo[b]furan (see Example 4, step A) and 62 mg (0.05 mmol) of Pd(Ph3)4, 1 mL of 2N aqueous sodium carbonate in 9 mL of toluene and 4 mL ethanol was heated to reflux. After complexion (TLC), water was added and the solution was extracted with ethyl acetate. The organic layer is dried over MgSO4 and after evaporation of the solvents, the crude oil was purified over a short silica plug (eluent: 10/90=ethyl acetate/hexane) to afford 2-acetyl-7-(3,5-diisopropyl-2-propoxyphenyl)-benzo[b]furan as a clear yellow pasty solid.

Aufarbeitung

  1. temperaturewas heated to reflux
  2. extractionthe solution was extracted with ethyl acetate
  3. dry with materialThe organic layer is dried over MgSO4
  4. customafter evaporation of the solvents
  5. customthe crude oil was purified over a short silica plug (eluent: 10/90=ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7bcad0ce85c549f58d3d77542cae7dfd
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348359B2

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