1-Bromopropane → 4-(4-Difluoromethoxy-3-methoxy-2-propoxy-phenyl)-indan-1-one

HRID 2171068Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2171068
[F:1][CH:2]([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[CH2:12][CH2:13][C:14]3=[O:19])=[C:6]([OH:20])[C:5]=1[O:21][CH3:22].C(=O)([O-])[O-].[K+].[K+].[CH2:30](Br)[CH2:31][CH3:32]>C(#N)C>[F:1][CH:2]([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[CH2:12][CH2:13][C:14]3=[O:19])=[C:6]([O:20][CH2:30][CH2:31][CH3:32])[C:5]=1[O:21][CH3:22]

Komponenten

5

Edukt 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 674685304-(4-(Difluoromethoxy)-2-hydroxy-3-methoxyphenyl)-2,3-dihydro-1H-inden-1-one

Produkt 1

HCID 545775914-(4-Difluoromethoxy-3-methoxy-2-propoxy-phenyl)-indan-1-oneAusbeute 33,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirring solution of 4-(4-(difluoromethoxy)-2-hydroxy-3-methoxyphenyl)-2,3-dihydro-1H-inden-1-one (80 mg, 0.25 mmol) in acetonitrile (10 mL) was added potassium carbonate (104 mg, 0.75 mmol) and propyl bromide (92 mg, 0.75 mmol) and the resultant reaction mixture was heated to 80° C. for 3 h. The reaction mixture was cooled to RT, filtered through celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 0-20% ethyl acetate in pet ether) to afford title compound as a solid (30 mg, 33.3%).

Aufarbeitung

  1. customthe resultant reaction mixture
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationfiltered through celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel, 0-20% ethyl acetate in pet ether)

Quellen und Nachweise

ORD-Eintrag
ord-1edd9e4c28ee426c8809e4d2ff08ceb9
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051290B2

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