Water → HCID 67468331, Verbindung

HRID 2171185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2171185
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH2:11][CH:12]2[CH2:14][CH2:13]2)[C:3]=1[O:15][CH2:16][O:17][CH3:18].C(=O)([O-])[O-].[Cs+].[Cs+].O.CC1(C)C(C)(C)OB([C:34]2[CH:42]=[CH:41][CH:40]=[C:39]3[C:35]=2[CH2:36][CH2:37][C:38]3=[O:43])O1>CN(C)C=O>[CH:12]1([CH2:11][O:10][C:4]2[C:3]([O:15][CH2:16][O:17][CH3:18])=[C:2]([C:34]3[CH:42]=[CH:41][CH:40]=[C:39]4[C:35]=3[CH2:36][CH2:37][C:38]4=[O:43])[CH:7]=[CH:6][C:5]=2[O:8][CH3:9])[CH2:14][CH2:13]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 220320882,3-Dihydro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-inden-1-oneHCID 67465591HCID 67465591, Verbindung

Produkt 1

HCID 67468331HCID 67468331, VerbindungAusbeute 51,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A stirring solution of 1-bromo-3-(cyclopropylmethoxy)-4-methoxy-2-(methoxymethoxy)benzene (3 g, 9.46 mmol) in dimethylformamide (50 mL) was purged with argon for 1 h, to this cesium carbonate (9.23 g, 28.39 mmol), water (3 mL), tetrakis triphenylphosphine palladium (546 mg, 0.472 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-one (2.93 g, 11.35 mmol) were added and the resultant reaction mixture was heated to 80° C. for 5 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, 0-20% ethyl acetate in pet ether) afforded 4-(3-(Cyclopropylmethoxy)-4-methoxy-2-(methoxymethoxy)phenyl)-2,3-dihydro-1H-inden-1-one as a solid (1.8 g, 51%).

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, 0-20% ethyl acetate in pet ether)

Quellen und Nachweise

ORD-Eintrag
ord-e5d3209a31a8438983b4ab4ca6746bd8
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051290B2

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