Sodium borohydride → 4'-(Hydroxymethyl)-3'-(trifluoromethyl)biphenyl-2-carbonitrile

HRID 1688466Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1688466
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]#[N:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][C:4]=1[C:17]([F:20])([F:19])[F:18])=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]#[N:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][C:4]=1[C:17]([F:18])([F:19])[F:20]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 866440264'-Formyl-3'-(trifluoromethyl)biphenyl-2-carbonitrile

Produkt 1

HCID 670098594'-(Hydroxymethyl)-3'-(trifluoromethyl)biphenyl-2-carbonitrileAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution (50 mL) of 4′-formyl-3′-(trifluoromethyl)biphenyl-2-carbonitrile (3.2 g) in methanol was added sodium borohydride (0.66 g), and the mixture was stirred at room temperature for 1 hr. After evaporation of the solvent under reduced pressure, the residue was extracted with water and ethyl acetate. The obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (3.1 g, 95%).

Aufarbeitung

  1. customAfter evaporation of the solvent under reduced pressure
  2. extractionthe residue was extracted with water and ethyl acetate
  3. washThe obtained ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4a0ef43e3ffe4de4a6e25a5e97851f0e
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148383B2

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