3-Bromopentane → N-(4-(2-ethyl-1-hydroxybutyl)phenyl)acetamide

HRID 1955069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1955069
Br[CH:2]([CH2:5][CH3:6])[CH2:3][CH3:4].[Mg].[CH:8]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=1)=[O:9].[NH4+].[Cl-]>CCOCC.C1COCC1>[CH2:3]([CH:2]([CH2:5][CH3:6])[CH:8]([C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:14][CH:15]=1)[OH:9])[CH3:4]

Komponenten

7

Edukt 4

HCID 157383-BromopentaneHCID 25517Ammonium ChlorideHCID 739424-AcetamidobenzaldehydeHCID 5462224Magnesium

Produkt 1

HCID 22603035N-(4-(2-ethyl-1-hydroxybutyl)phenyl)acetamideAusbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3-bromopentane (0.331 mol) in (C2H5)2O (200 ml) was added dropwise to a solution of magnesium turnings (0.331 mol) in (C2H5)2O, the mixture was stirred at RT for 2 hours and then cooled to 0° C. A solution of N-(4-formylphenyl)acetamide (0.11 mol) in THF (400 ml) was added dropwise and the mixture was stirred for 10 minutes. The mixture was poured into aqueous NH4Cl and extracted with EtOAc. The organic layer was dried, filtered off and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 97/3/0.1). The pure fractions were collected and evaporated, yielding 13.5 g (52%) of (±)-N-[4-(2-ethyl-1-hydroxybutyl)phenyl]acetamide (interm. 13).

Aufarbeitung

  1. temperaturecooled to 0° C
  2. stirringthe mixture was stirred for 10 minutes
  3. extractionextracted with EtOAc
  4. customThe organic layer was dried
  5. filtrationfiltered off
  6. customthe solvent evaporated
  7. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 97/3/0.1)
  8. customThe pure fractions were collected
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f965716fd5254ae8bfa2df2da93a957b
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06124330

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