Water → Methyl 4-(cyclopropylidenemethyl)benzoate

HRID 7356

Reaktionsgleichung

[H-].[Na+].[Br-].[CH:4]1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:6][CH2:5]1.[CH3:26][O:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([CH:36]=O)=[CH:32][CH:31]=1)=[O:29].O>O1CCCC1>[C:4]1(=[CH:36][C:33]2[CH:34]=[CH:35][C:30]([C:28]([O:27][CH3:26])=[O:29])=[CH:31][CH:32]=2)[CH2:6][CH2:5]1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

To a suspension of sodium hydride (60%, 0.27 g) in tetrahydrofuran (40 mL) was added cyclopropyltriphenylphosphonium bromide (2.6 g), and the mixture was stirred at 70° C. for 2 hours. To the reaction mixture was added methyl terephthalaldehydate (1.0 g), and the mixture was stirred at 70° C. for 7 days. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/dichloromethane=1/1) to give methyl 4-(cyclopropylidenemethyl)benzoate (0.80 g).

Aufarbeitung

stirringthe mixture was stirred at 70° C. for 7 days
extractionthe mixture was extracted with diethyl ether
washThe organic layer was washed with water and brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure
customThe residue was purified by column chromatography on silica gel (eluent: hexane/dichloromethane=1/1)

Quellen und Nachweise

ORD-Eintrag: ord-b693a864a5f84c91904645550a8b9dac
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07087579B2

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