Sodium borohydride → HCID 59370515, Verbindung

HRID 2046651Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2046651
[F:1][C:2]1[C:9]([CH:10]=[O:11])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.FC1C=CC(C#N)=C(C(F)(F)F)C=1C=O.[BH4-].[Na+]>O1CCCC1.[Cl-].[Na+].O>[F:1][C:2]1[C:9]([CH2:10][OH:11])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:12]([F:13])([F:14])[F:15])[CH:3]=1

Komponenten

6

Edukt 3

HCID 4311764Sodium borohydrideHCID 713331064-Fluoro-3-formyl-2-(trifluoromethyl)benzonitrileHCID 862572524-Fluoro-5-formyl-2-(trifluoromethyl)benzonitrile

Produkt 1

HCID 59370515HCID 59370515, VerbindungAusbeute 44,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution (15 mL) of a mixture (1.01 g) of 4-fluoro-5-formyl-2-(trifluoromethyl)benzonitrile and 4-fluoro-3-formyl-2-(trifluoromethyl)benzonitrile (3:1) in tetrahydrofuran was added sodium borohydride (400 mg) at 0° C., and the mixture was stirred at room temperature for 12 hr. Saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate=5:1→1:4) to give the title compound as a yellow oil (yield: 456 mg).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate=5:1→1:4)

Quellen und Nachweise

ORD-Eintrag
ord-e29e1666441f44a3bd3e3e7fb7beeb73
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592452B2

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