Sodium borohydride → trans-3-(2-Pyridyl)cyclopentanol

HRID 655144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 655144
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8]1.[BH4-].[Na+]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@H:7]1[CH2:11][CH2:10][C@H:9]([OH:12])[CH2:8]1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 594861153-(2-Pyridyl)cyclopentan-1-one

Produkt 1

HCID 67133971trans-3-(2-Pyridyl)cyclopentanolAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 3-(2-pyridyl)cyclopentan-1-one (3.17 g, 19.7 mmol) in MeOH (80 ml) was added portionwise NaBH4 (745 mg. 19.7 mmol) at 0° C., and stirred for 2 h at room temperature. The reaction mixture was poured into ice-water and then extracted with EtOAc. The organic layer was dried over anhyd Na2SO4 followed by the removal of solvent. The crude product was purified by column chromatography (Hexane/EtOAc=1/1→1/3) to yield trans-3-(2-pyridyl)cyclopentanol (965 mg, 30%) as colorless oil.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhyd Na2SO4
  3. customfollowed by the removal of solvent
  4. customThe crude product was purified by column chromatography (Hexane/EtOAc=1/1→1/3)

Quellen und Nachweise

ORD-Eintrag
ord-55a01f475c14459c984030718130a64c
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071591B2

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