Lithium borohydride → 2-(4-Bromo-2-methyl-phenyl)-4-hydroxy-butyronitrile

HRID 503908Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 503908
[BH4-].[Li+].C[O:4][C:5](=O)[CH2:6][CH:7]([C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=1[CH3:17])[C:8]#[N:9].OS([O-])(=O)=O.[K+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([CH:7]([CH2:6][CH2:5][OH:4])[C:8]#[N:9])=[C:11]([CH3:17])[CH:12]=1

Komponenten

5

Edukt 3

HCID 4148881Lithium borohydrideHCID 668771313-(4-Bromo-2-methyl-phenyl)-3-cyano-propionic acid methyl esterHCID 86586342KHSO4 Na2SO4

Produkt 1

HCID 594283342-(4-Bromo-2-methyl-phenyl)-4-hydroxy-butyronitrileAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Lithium borohydride (4.99 g, 0.2290 mol) was added to a room temperature solution of 3-(4-bromo-2-methyl-phenyl)-3-cyano-propionic acid methyl ester (43.08 g, 0.1527 mol) in THF (500 mL) and the reaction mixture was stirred overnight. The reaction mixture was cooled to 0° C., and a solution of 10% KHSO4/Na2SO4 was slowly added until pH 1-2 was reached. The resulting mixture was extracted with EtOAc, and the combined organic extracts were washed with water and brine, dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc, 7/3) to give 27.3 g (87% yield) of 2-(4-bromo-2-methyl-phenyl)-4-hydroxy-butyronitrile as a white solid.

Aufarbeitung

  1. extractionThe resulting mixture was extracted with EtOAc
  2. washthe combined organic extracts were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified via flash chromatography (hexane/EtOAc, 7/3)

Quellen und Nachweise

ORD-Eintrag
ord-9e7375483a8e47399aedbb2bb604d1d2
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776910B2

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