Sodium borohydride → 4-(3-Isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-benzyl alcohol

HRID 1007478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1007478
[BH4-].[Na+].[CH:3]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][C:16]3[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][C:17]=3[C:28]([F:31])([F:30])[F:29])[CH:13]=2)[NH:8][CH:7]=1)([CH3:5])[CH3:4]>CO>[CH:3]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][C:16]3[C:23]([C:24]([F:25])([F:27])[F:26])=[CH:22][C:19]([CH2:20][OH:21])=[CH:18][C:17]=3[C:28]([F:31])([F:29])[F:30])[CH:13]=2)[NH:8][CH:7]=1)([CH3:5])[CH3:4]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 226698054-(3-Isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-benzaldehyde

Produkt 1

HCID 601106964-(3-Isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-benzyl alcohol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

0.27 g (7.22 mmol) of sodium borohydride is added to a solution of 1.0 g (2.41 mmol) of aldehyde derivative from Example V in 20 ml of methanol in 4 portions at room temperature and the mixture is stirred for 1 hour. Afterwards the reaction solution is concentrated to one half, 60 ml of water are added and the mixture is concentrated until methanol is completely evaporated in a rotary evaporator. The aqueous phase is extracted three times with ethyl acetate, the combined organic phases are washed with sodium chloride solution, dried and concentrated, and the residue is dried in a high vacuum.

Aufarbeitung

  1. concentrationAfterwards the reaction solution is concentrated to one half, 60 ml of water
  2. additionare added
  3. concentrationthe mixture is concentrated until methanol
  4. customis completely evaporated in a rotary evaporator
  5. extractionThe aqueous phase is extracted three times with ethyl acetate
  6. washthe combined organic phases are washed with sodium chloride solution
  7. customdried
  8. concentrationconcentrated
  9. customthe residue is dried in a high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8b8c57b170a142b3bb4a5811866e2614
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06794406B2

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