Water → Ethyl 4-({5-[3-(trifluoromethyl)phenyl]furan-2-yl}methyl)benzoate

HRID 1257479

Reaktionsgleichung

Reaktionsgleichung von HRID 1257479
[I-].[Na+].Cl[Si](C)(C)C.O[CH:9]([C:21]1[O:22][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=2)=[CH:24][CH:25]=1)[C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=1.O>C(#N)C>[F:34][C:32]([F:33])([F:35])[C:28]1[CH:27]=[C:26]([C:23]2[O:22][C:21]([CH2:9][C:10]3[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=3)=[CH:25][CH:24]=2)[CH:31]=[CH:30][CH:29]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 66939737Ethyl 4-(hydroxy{5-[3-(trifluoromethyl)phenyl]furan-2-yl}methyl)benzoate

Produkt 1

HCID 66939680Ethyl 4-({5-[3-(trifluoromethyl)phenyl]furan-2-yl}methyl)benzoateAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

Sodium iodide (0.49 g) was suspended in acetonitrile (2 mL), and the suspension was cooled in an ice bath. Chlorotrimethylsilane (0.42 mL), and then a solution of the compound (0.26 g) obtained in Example 222b in acetonitrile (2 mL) were added. The reaction mixture was stirred at the same temperature for 30 min, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (0.22 g) as an oil.

Aufarbeitung

  1. temperaturethe suspension was cooled in an ice bath
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-9b2caf62981d42d98926b957a431c752
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461348B2

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