Sodium borohydride → 3-(5-Trifluoromethylbenzofur-7-yl)-2-butanol

HRID 1824970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1824970
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH:12]([CH3:16])[C:13](=[O:15])[CH3:14])[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1.[BH4-].[Na+]>C(O)C>[F:17][C:2]([F:1])([F:18])[C:3]1[CH:4]=[C:5]([CH:12]([CH3:16])[CH:13]([OH:15])[CH3:14])[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 221449223-(5-Trifluoromethylbenzofur-7-yl)-2-butanone

Produkt 1

HCID 221448643-(5-Trifluoromethylbenzofur-7-yl)-2-butanolAusbeute 45,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 0.09 gm (0.35 mMol) 3-(5-trifluoromethylbenzofur-7-yl)-2-butanone in ethanol was cooled to 0° C. To this solution was added 0.013 gm (0.35 mMol) sodium borohydride and the resulting mixture stirred for 30 minutes. The reaction mixture was then allowed to warm to room temperature and was concentrated under reduced pressure. The residue was taken up in ethyl acetate and washed sequentially with 0.1 N hydrochloric acid, water, and saturated aqueous sodium chloride. The remaining organic phase was concentrated under reduced pressure and the residue subjected to silica gel chromatography, eluting with 30% ethyl acetate in hexane. Fractions containing product were combined and concentrated under reduced pressure to provide 0.041 gm (45%) of the desired compound.

Aufarbeitung

  1. concentrationwas concentrated under reduced pressure
  2. washwashed sequentially with 0.1 N hydrochloric acid, water, and saturated aqueous sodium chloride
  3. concentrationThe remaining organic phase was concentrated under reduced pressure
  4. washeluting with 30% ethyl acetate in hexane
  5. additionFractions containing product
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5d44e87683e240ccb6b7652de52247e5
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07045545B1

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