Ethanol → Methyl 3-(4-((2'-ethoxybiphenyl-3-yl)methoxy)phenyl)propanoate

HRID 2422288

Reaktionsgleichung

Reaktionsgleichung von HRID 2422288
Br[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=1.[CH2:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O)[CH3:23].C(=O)([O-])[O-].[K+].[K+].C(O)C>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH2:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:2]1[CH:21]=[CH:20][CH:19]=[C:4]([CH2:5][O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=2)[CH:3]=1)[CH3:23]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 2734902(2-Ethoxyphenyl)boronic acidHCID 23136270Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoate

Produkt 1

HCID 23083192Methyl 3-(4-((2'-ethoxybiphenyl-3-yl)methoxy)phenyl)propanoateAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of methyl 3-[4-[(3-bromobenzyl)oxy]phenyl]propanoate (0.30 g, 0.86 mmol), 2-ethoxyphenylboronic acid (0.16 g, 0.95 mmol), tetrakistriphenylphosphine palladium (40 mg, 0.034 mmol), 2N potassium carbonate aqueous solution (0.3 mL), ethanol (0.3 mL) and toluene (3 mL) was heated under reflux overnight under an argon atmosphere. The reaction mixture was cooled, diluted with ethyl acetate, washed with water, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-2/1) to give methyl 3-(4-((2′-ethoxybiphenyl-3-yl)methoxy)phenyl)propanoate (0.21 g, 63%) as a colorless oil.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux overnight under an argon atmosphere
  3. temperatureThe reaction mixture was cooled
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-2/1)

Quellen und Nachweise

ORD-Eintrag
ord-a3f0659dc5fd4a16ba8c2dbd58ae8010
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960369B2

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