Triethylamine → 4-Formylcinnamic acid tert-butyl ester

HRID 556280

Reaktionsgleichung

Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+].[C:22]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])(=[O:25])[CH:23]=[CH2:24]>CN(C=O)C.O.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:27]([O:26][C:22](=[O:25])[CH:23]=[CH:24][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)([CH3:30])([CH3:29])[CH3:28]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A solution of 4-bromo benzaldehyde (2 g, 10.8 mmol) in DMF (50 ml) and triethylamine (3.4 ml, 27 mmol) was degassed flushing N2 for 30 min. PPh3 (141 mg, 0.54 mmol), Pd(OAc)2 (48.4 mg, 0.21 mmol), NaHCO3 (1.84 g, 21.6 mmol) and tert-butyl acrylate (1.58 ml, 10.8 mmol) were added and the resulting mixture was heated to reflux for 3 h. Additional Pd(OAc)2 (24 mg) was added and the mixture was heated to 100° C. for 1 h. The solution was diluted with H2O and extracted with Et2O. The organic layer was dried over Na2SO4 and the solvent was evaporated under vacuo to give the crude product that was triturated in isopropyl ether to give 1.6 g of 3-(4-formyl-phenyl)-acrylic acid tert-butyl ester.

Aufarbeitung

customflushing N2 for 30 min
temperaturethe resulting mixture was heated
temperatureto reflux for 3 h
extractionextracted with Et2O
dry with materialThe organic layer was dried over Na2SO4
customthe solvent was evaporated under vacuo
customto give the crude product that
customwas triturated in isopropyl ether

Quellen und Nachweise

ORD-Eintrag: ord-4c0e5a8c3bc640fb8024f6cba150baa7
Quelldatensatz: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08058273B2

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