Sodium Chloride → 4-[2-[2,3-Dihydro-2-(4-fluorophenyl)-2-methyl-3-oxo-5-furanyl]ethenyl]benzonitrile

HRID 359383

Reaktionsgleichung

Reaktionsgleichung von HRID 359383
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].[CH3:11][C:12]1([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:16](=[O:17])[CH:15]=[C:14]([CH3:18])[O:13]1.[OH-].[Na+].[Cl-].[Na+]>C(O)C>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:12]2([CH3:11])[C:16](=[O:17])[CH:15]=[C:14]([CH:18]=[CH:7][C:6]3[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[O:13]2)=[CH:20][CH:21]=1

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 660424-CyanobenzaldehydeHCID 150867042-(4-Fluorophenyl)-2,5-dimethylfuran-3(2H)-one

Produkt 1

HCID 536486264-[2-[2,3-Dihydro-2-(4-fluorophenyl)-2-methyl-3-oxo-5-furanyl]ethenyl]benzonitrileAusbeute 38,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of p-cyanobenzaldehyde (1.6 g, 11.8 mM) and 2,5-dimethyl-2-(4-fluorphenyl)-3(2H)-furanone (2.0 g, 9.8 mM) in ethanol (75 mL), was added 1N aqueous sodium hydroxide (1.0 mL, 1 mM). After the reaction solution was stirred at room temperature for two days, saturated aqueous sodium chloride (400 mL) was added. The aqueous layer was extracted with dichloromethane (3×100 mL). The combined dichloromethane extracts were washed with saturated aqueous sodium chloride (50 mL), dried over MgSO4, filtered and concentrated to give an orange liquid. The crude product was purified by chromatography (silica gel, pet. ether-ethyl acetate) to give a yellow crystalline solid (1.2 g, 38% yield), m.p. 140°-142° C.

Aufarbeitung

  1. extractionThe aqueous layer was extracted with dichloromethane (3×100 mL)
  2. washThe combined dichloromethane extracts were washed with saturated aqueous sodium chloride (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an orange liquid
  7. customThe crude product was purified by chromatography (silica gel, pet. ether-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-512b3fe8570b43ae928e1f12c97eb2d0
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US05001126

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