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

HRID 1271317Notes

Reaction equation

HRID 1271317 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

HCID 22603035N-(4-(2-ethyl-1-hydroxybutyl)phenyl)acetamideYield 52.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-90738b8ececc47f5b70cef8d76539038
Source dataset
uspto-grants-2007_04
Patent number
US07205312B2

Reaction notes

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