Sodium borohydride → 7-(2-Hydroxyethyl)-4-phenylquinoline-2-carbonitrile

HRID 2422569Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422569
[O:1]=[CH:2][CH2:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:9][C:10]([C:14]#[N:15])=[N:11]2)=[CH:6][CH:5]=1.[BH4-].[Na+]>C1COCC1.CO>[OH:1][CH2:2][CH2:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:9][C:10]([C:14]#[N:15])=[N:11]2)=[CH:6][CH:5]=1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 597749037-(2-Oxoethyl)-4-phenylquinoline-2-carbonitrile

Produkt 1

HCID 597748837-(2-Hydroxyethyl)-4-phenylquinoline-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 7-(2-oxoethyl)-4-phenylquinoline-2-carbonitrile (1.5 g, 5.5 mmol) in THF (30 mL) and MeOH (10 mL) was added portionwise at 0° C. sodium borohydride (320 mg, 8.4 mmol). The mixture was stirred overnight at rt. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 concentrated under reduced pressure and purified on silica gel (eluting with ethyl acetate/hexanes, 1:1) to give the title compound. MS (+ESI): 275 (M+H)+.

Aufarbeitung

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. custompurified on silica gel (eluting with ethyl acetate/hexanes, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-bac19b0c6d7140f38ba4ea91741ed8e0
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960409B2

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