Cesium carbonate → 4-(3-Hydroxy-2,4-dimethoxyphenyl)-2,3-dihydro-1H-inden-1-one

HRID 2171141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2171141
CC1(C)C(C)(C)OB([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH2:11][CH2:12][C:13]3=[O:18])O1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:27]1[C:28]([O:36][CH3:37])=[C:29]([OH:35])[C:30]([O:33][CH3:34])=[CH:31][CH:32]=1>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:35][C:29]1[C:30]([O:33][CH3:34])=[C:31]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH2:11][CH2:12][C:13]3=[O:18])[CH:32]=[CH:27][C:28]=1[O:36][CH3:37]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 150736683-Bromo-2,6-dimethoxyphenolHCID 220320882,3-Dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-inden-1-one

Produkt 1

HCID 701704534-(3-Hydroxy-2,4-dimethoxyphenyl)-2,3-dihydro-1H-inden-1-oneAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A stirring solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-one (3 g, 12.87 mmol) in dimethylformamide (30 mL) was purged with argon for 1 h, to this cesium carbonate (12.58 g, 38.61 mmol), Pd (PPh3)4 (743 mg, 0.64 mmol) and 3-bromo-2,6-dimethoxyphenol (3.32 g, 12.87 mmol) were added and the resultant reaction mixture was heated to 80-90° C. for 16 h. The reaction mixture was cooled to RT, filtered through celite and the filtrate was diluted with water and extracted with ethyl acetate (3×). The combined ethyl acetate layers were washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel, 0-10% ethyl acetate in pet ether) afforded the title compound as a solid (1.5 g, 41%).

Aufarbeitung

  1. additionwere added
  2. customthe resultant reaction mixture
  3. temperatureThe reaction mixture was cooled to RT
  4. filtrationfiltered through celite
  5. additionthe filtrate was diluted with water
  6. extractionextracted with ethyl acetate (3×)
  7. washThe combined ethyl acetate layers were washed with brine
  8. dry with materialdried over anhydrous sodium sulphate
  9. concentrationconcentrated under reduced pressure
  10. customPurification of the residue by column chromatography (silica gel, 0-10% ethyl acetate in pet ether)

Quellen und Nachweise

ORD-Eintrag
ord-a5a5a8083d734b7e84b4219bb5292ae3
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051290B2

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