Sodium Carbonate → 4-{2-[4-(t-Butyldimethylsilanyloxymethyl)-2-methyl-4,5-dihydrooxazol-4-yl]ethyl}-biphenyl-4-carbaldehyde

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Reaktionsgleichung

Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2([CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:14][O:13][C:12]([CH3:15])=[N:11]2)=[CH:4][CH:3]=1.[C:25]([O-:28])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.O.CCOC(C)=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>[Si:18]([O:17][CH2:16][C:10]1([CH2:9][CH2:8][C:5]2([CH:25]=[O:28])[CH:6]=[CH:7][C:2]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:3][CH2:4]2)[CH2:14][O:13][C:12]([CH3:15])=[N:11]1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

The mixture of 4-[2-(4-bromophenyl)ethyl]-4-(t-butyldimethylsilanyloxymethyl)-2-methyl-4,5-dihydrooxazole (2 mmol), 4-fomylphenylboronic acid (2.4 mmol), Pd(PPh3)4 (0.2 mmol) and Na2CO3 (9.6 mmol) in toluene (5 mL), EtOH (1.5 mL) and H2O (5 mL) is stirred at 90° C. for 5 h. It is diluted with H2O (15 mL) and EtOAc (15 mL) and the organic phase is washed with brine and dried over Na2SO4. After concentration, the crude product is purified by column chromatography using EtOAc/hexane (1/4) to give the desired product as a white solid. MS: (ES+): 438.2 (M+1)+.

Aufarbeitung

washthe organic phase is washed with brine
dry with materialdried over Na2SO4
concentrationAfter concentration
customthe crude product is purified by column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-e8980b17e19044bab5848ac7399bd71e
Quelldatensatz: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07169817B2

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