Ethyl Acetate → Methyl 3-(4-methoxybiphenylyl)acrylate

HRID 12991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 12991
Br[C:2]1[CH:13]=[CH:12][C:5]([CH:6]=[CH:7][C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.CO[C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C[CH2:26][O:27]C(C)=O>C1(C)C=CC=CC=1.CCO.C([O-])([O-])=O.[Na+].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:26][O:27][C:13]1[CH:2]=[CH:3][C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:5]([CH:6]=[CH:7][C:8]([O:10][CH3:11])=[O:9])[CH:12]=1

Komponenten

9

Edukt 3

HCID 8857Ethyl AcetateHCID 201262(4-Methoxyphenyl)boronic acidHCID 8167732-Propenoic acid, 3-(4-bromophenyl)-, methyl ester

Produkt 1

HCID 68585185Methyl 3-(4-methoxybiphenylyl)acrylate

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Versuchsvorschrift

200 mg (0.83 mmol) of methyl 4-bromocinnamate were dissolved in dry toluene, added with 29 mg (0.025 mmol) of Pd(PPh3)4, a solution of 152 mg (0.91 mmol) of 4-methoxybenzeneboronic acid in 0.5 ml of EtOH, 1.66 ml of 2M Na2CO3 in water, and refluxed 2 h. Addition of EtOAc, washing with water, then with brine, filtration and flash chromatography (Merck silicagel) with Hexane/EtOAc mixtures from 95/5 to 8/2 gave 112 mg of methyl 3-(4-methoxybiphenylyl)acrylate, mp. 175-177° C.

Aufarbeitung

  1. washwashing with water
  2. filtrationwith brine, filtration and flash chromatography (Merck silicagel) with Hexane/EtOAc mixtures from 95/5 to 8/2

Quellen und Nachweise

ORD-Eintrag
ord-676ac36e85f14d97aa1eb9f2734587ed
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728039B2

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