Sodium hydride → 5-(2-tert-Butoxycarbonylethenyl)furan-2-carboxylic acid benzyl ester

HRID 517334

Reaktionsgleichung

[C:1]([O:5][C:6](=[O:16])[CH2:7]P(OCC)(OCC)=O)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:19]([O:26][C:27]([C:29]1[O:30][C:31]([CH:34]=O)=[CH:32][CH:33]=1)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[CH2:19]([O:26][C:27]([C:29]1[O:30][C:31]([CH:34]=[CH:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:16])=[CH:32][CH:33]=1)=[O:28])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A solution of diethylphosphonoacetic acid tert-butyl ester (1.54 g, 6.09 mmol) in tetrahydrofuran (3 mL) was added dropwise to a suspension of 60% sodium hydride (0.19 g, 4.87 mmol) in tetrahydrofuran (50 mL) with stirring at 0° C. After stirring at room temperature for 20 minutes, a solution of 5-formyl-2-furancarboxylic acid benzyl ester (1.0 g, 4.06 mmol) in tetrahydrofuran (3 mL) was added, and the mixture was stirred at room temperature for 1 hour. The mixture was worked up according to a conventional method, and the object product was extracted by column chromatography (10-30% ethyl acetate/hexane mixed solvent) to give the title compound (1.17 g)

Aufarbeitung

stirringAfter stirring at room temperature for 20 minutes
stirringthe mixture was stirred at room temperature for 1 hour
extractionthe object product was extracted by column chromatography (10-30% ethyl acetate/hexane mixed solvent)

Quellen und Nachweise

ORD-Eintrag: ord-4895dd6cbfbd476f85f7cc576ebab708
Quelldatensatz: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09115107B2

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