Sodium borohydride → 1-{6-[4-(Trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol

HRID 1391727

Reaktionsgleichung

Reaktionsgleichung von HRID 1391727
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([C:15](=[O:20])[CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[BH4-].[Na+]>C1COCC1.O>[F:21][C:2]([F:1])([F:22])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[C:13]([CH:15]([OH:20])[CH2:16][CH2:17][CH2:18][CH3:19])[CH:12]=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 586299011-{6-[4-(Trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanone

Produkt 1

HCID 586298221-{6-[4-(Trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanolAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanone (2.80 g, 9.11 mmol) in THF (61 mL) at 0° C. (ice/water bath) was treated drop-wise with a mixture of sodium borohydride (689 mg, 18.21 mmol) in water (11 mL) over 5-10 minutes. The resulting mixture was stirred at this temperature for 2.5 hours and was then partitioned between EtOAc (200 mL) and water (200 mL) and the layers separated. The aqueous was re-extracted with EtOAc (200 mL) and the combined organic layer washed with brine (250 mL), dried (MgSO4), filtered and reduced. Purification by Biotage™ chromatography (silica) eluting with cyclohexane:EtOAc (gradient 20:1 to 5:1) afforded the title compound as a colourless oil (2.81 g).

Aufarbeitung

  1. additionwas treated drop-wise
  2. customwas then partitioned between EtOAc (200 mL) and water (200 mL)
  3. customthe layers separated
  4. extractionThe aqueous was re-extracted with EtOAc (200 mL)
  5. washthe combined organic layer washed with brine (250 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customPurification by Biotage™ chromatography (silica)
  9. washeluting with cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-beda19d4626a4e8c874d260255c78966
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07338960B2

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