Potassium Carbonate → Methyl 7-(3,4-methylenedioxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate

HRID 1277255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1277255
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1.B([O-])([O-])O[C:19]1[CH:24]=[CH:23][C:22]2[O:25][CH2:26][O:27][C:21]=2[CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O>[CH2:26]1[O:27][C:21]2[CH:20]=[CH:19][C:24]([C:2]3[CH:3]=[CH:4][C:5]4[S:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=4[CH:16]=3)=[CH:23][C:22]=2[O:25]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 18472606HCID 18472606, VerbindungHCID 867561803,4-Methlenedioxyphenyl borate

Produkt 1

HCID 18472255Methyl 7-(3,4-methylenedioxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylateAusbeute 90,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 86587398Ethanol toluene waterLösungsmittel

Versuchsvorschrift

Under argon atmosphere, a mixture of methyl 7-bromo-2,3-dihydro-1-benzothiepine-4-carboxylate (1.5 g), 3,4-methylenedioxyphenyl borate (0.92 g) and potassium carbonate (1.39 g) in toluene/ethanol/water (50/5/5 ml) was stirred at room temperaturel hours. To the mixture was added tetrakistriphenylphosphine palladium (0.29 g), and the mixture was refluxed for 16 hours and cooled. The mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the residue was purified with column chromatography (ethyl acetate/hexane=1:2) to give pale yellow crystals of methyl 7-(3,4-methylenedioxyphenyl)-2,3-dihydro-1-benzo-thiepine-4-carboxylate (1.55 g).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 16 hours
  2. temperaturecooled
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationUnder reduced pressure, the mixture was concentrated
  7. customthe residue was purified with column chromatography (ethyl acetate/hexane=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-20a2927add9e4b81af1d9fa64ba0dbcc
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06166006

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