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

HRID 2224638ノート

反応式

HRID 2224638 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

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-formyl-phenyl)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).

後処理

  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

出典と根拠

ORDレコード
ord-2f3d43809ad24efcba765c426972a8cf
出典データセット
uspto-grants-2008_05
特許番号
US07378433B2

反応ノート

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