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Water → Methyl 8-[4-(2-propoxyethoxy)phenyl]-1-propyl-1,2,3,4-tetrahydro-1-benzazocine-5-carboxylate

HRID 2222855
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2222855
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:12]([CH2:13][CH2:14][CH3:15])[CH2:11][CH2:10][CH2:9][C:8]([C:16]([O:18][CH3:19])=[O:17])=[CH:7][C:6]=2[CH:20]=1.[CH2:21]([O:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32](OB(O)O)=[CH:31][CH:30]=1)[CH2:22][CH2:23]C.C(=O)([O-])[O-].[K+].[K+].O>C1(C)C(CCO)=CC=CC=1.O>[CH2:21]([O:25][CH2:26][CH2:27][O:28][C:29]1[CH:30]=[CH:31][C:32]([C:2]2[CH:3]=[CH:4][C:5]3[N:12]([CH2:13][CH2:14][CH3:15])[CH2:11][CH2:10][CH2:9][C:8]([C:16]([O:18][CH3:19])=[O:17])=[CH:7][C:6]=3[CH:20]=2)=[CH:33][CH:34]=1)[CH2:22][CH3:23]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 230910874-(2-Butoxyethoxy)phenylboric acidHCID 68650111Methyl 8-bromo-1-propyl-1,2,3,4-tetrahydro-1-benzazocine-5-carboxylate

Produkt 1

HCID 68650188Methyl 8-[4-(2-propoxyethoxy)phenyl]-1-propyl-1,2,3,4-tetrahydro-1-benzazocine-5-carboxylateAusbeute 56,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 66602552Toluene-ethanol waterLösungsmittel

Versuchsvorschrift

Under argon atmosphere, a mixture of methyl 8-bromo-1-propyl-1,2,3,4-tetrahydro-1-benzazocine-5-carboxylate (1.5 g), 4-(2-butoxyethoxy)phenyl boric acid (1.29 g) and potassium carbonate (1.23 g) in toluene-ethanol-water (45-4.5-4.5 ml) was stirred at room temperature for 1 hour. To the reaction system was added tetrakis-(triphenylphosphine)palladium (0.26 g) was added, and the mixture was refluxed for 4 hours. After cooling to room temperature, water was added and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried with magnesium sulfate. After concentration under reduced pressure, the residue was separated to purify by column chromatography (ethyl acetate:hexane=1:49→1:19→1:9) to give methyl 8-[4-(2-propoxyethoxy)phenyl]-1-propyl-1,2,3,4-tetrahydro-1-benzazocine-5-carboxylate (1.10 g) as a yellow oily material.

Aufarbeitung

  1. additionwas added
  2. temperaturethe mixture was refluxed for 4 hours
  3. temperatureAfter cooling to room temperature
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationAfter concentration under reduced pressure
  8. customthe residue was separated
  9. customto purify by column chromatography (ethyl acetate:hexane=1:49→1:19→1:9)

Quellen und Nachweise

ORD-Eintrag
ord-3de50332c5944aaca4f414cd263bd973
Quelldatensatz
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07371772B2

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