Potassium Carbonate → Methyl 7-(5-methyl-2-thienyl)-2,3-dihydro-1-benzoxepine-4-carboxylate

HRID 566089Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 566089
Br[C:2]1[CH:3]=[CH:4][C:5]2[O: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[S:20][C:21]([CH3:24])=[CH:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O>[CH3:24][C:21]1[S:20][C:19]([C:2]2[CH:3]=[CH:4][C:5]3[O:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=3[CH:16]=2)=[CH:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 22990005Methyl 7-bromo-2,3-dihydro-1-benzooxepine-4-carboxylateHCID 867561815-Methyl-2-thienyl borate

Produkt 1

HCID 18472362Methyl 7-(5-methyl-2-thienyl)-2,3-dihydro-1-benzoxepine-4-carboxylateAusbeute 58,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 86587398Ethanol toluene waterLösungsmittel

Versuchsvorschrift

In toluene/ethanol/water (10/1/1) (24 ml) was dissolved methyl 7-bromo-2,3-dihydro-1-benzoxepine-4-carboxylate (560 mg), and to the mixture were added 5-methyl-2-thienyl borate (875 mg) and potassium carbonate (1.56 g). The mixture was stirred at room temperature for 30 minutes. To the mixture was added tetrakistriphenylphosphine palladium (260 mg), and the mixture was stirred at 100° C. for 24 hours and cooled to room temperature. The mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was removed, and the resulting residue was purified with silica gel column chromatography (hexane/acetone=12/1) to give methyl 7-(5-methyl-2-thienyl)-2,3-dihydro-1-benzoxepine-4-carboxylate (345 mg).

Aufarbeitung

  1. stirringthe mixture was stirred at 100° C. for 24 hours
  2. temperaturecooled to room temperature
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customUnder reduced pressure, the solvent was removed
  7. customthe resulting residue was purified with silica gel column chromatography (hexane/acetone=12/1)

Quellen und Nachweise

ORD-Eintrag
ord-566937a36ce74f3eab520edf9aac10c6
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06172061B2

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