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

HRID 566077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 566077
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]([O:25][CH3:26])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([C:2]2[CH:3]=[CH:4][C:5]3[S:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=3[CH:16]=2)=[CH:20][CH:21]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 18472606HCID 18472606, VerbindungHCID 86645335(4-Methoxyphenyl)borate

Produkt 1

HCID 18472336Methyl 7-(4-methoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylateAusbeute 85,5 %

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), 4-methoxyphenyl borate (0.84 g) and potassium carbonate (1.39 g) in toluene/ethanol/water (50/5/5 ml) was stirred at room temperature for 1 hour. To the mixture was added tetrakistriphenylphosphine palladium (0.17 g), and the mixture was refluxed for 24 hours and then 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=1:15→1:9→1:4→1:2) to give pale yellow crystals of methyl 7-(4-methoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate (1.40 g).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 24 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=1:15→1:9→1:4→1:2)

Quellen und Nachweise

ORD-Eintrag
ord-ad9fa92ca3e04b928532c246fc187d7a
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06172061B2

Notizen zur Reaktion

Wird geladen…