Sodium Hydroxide → 2,2-Dimethyl-5-[2-(4-fluorophenyl)ethenyl]-3(2H)-furanone

HRID 359357

Reaktionsgleichung

[CH3:1][C:2]1([CH3:9])[C:6](=[O:7])[CH:5]=[C:4]([CH3:8])[O:3]1.[F:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.[OH-].[Na+]>C(O)C.[Cl-].[Na+].O>[CH3:1][C:2]1([CH3:9])[C:6](=[O:7])[CH:5]=[C:4]([CH:8]=[CH:15][C:14]2[CH:17]=[CH:18][C:11]([F:10])=[CH:12][CH:13]=2)[O:3]1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of 2,2,5-trimethyl-3(2H)-furanone (2.0 g, 15.9 mM) and 4-fluorobenzaldehyde (1.6 g, 13.2 mM) in ethanol (100 mL), was added 1N aqueous sodium hydroxide (1.6 mL, 1.6 mM). The reaction solution was heated at 50° C. for four hours. After the reaction solution was cooled to room temperature and diluted with saturated aqueous sodium chloride (200 mL) and water (200 mL), the aqueous solution was extracted with diethyl ether (2×100 mL). The combined ethereal extracts were washed with saturated aqueous sodium chloride (25 mL), dried over magnesium sulfate, filtered and concentrated at reduced pressure to afford a dark yellow crystalline solid. The crude product was recrystallized from hexane to give light yellow crystals (1.8 g, 45% yield), m.p. 55°-57° C.

Aufarbeitung

temperatureAfter the reaction solution was cooled to room temperature
extractionthe aqueous solution was extracted with diethyl ether (2×100 mL)
washThe combined ethereal extracts were washed with saturated aqueous sodium chloride (25 mL)
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated at reduced pressure
customto afford a dark yellow crystalline solid
customThe crude product was recrystallized from hexane

Quellen und Nachweise

ORD-Eintrag: ord-f7c4370264ef4afa9c17b83d3ff7a798
Quelldatensatz: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05001126

Verknüpfte Notizen

Wird geladen…