1-Bromopropane → N-[4-(1-hydroxybutyl)phenyl]acetamide

HRID 1086193ノート

反応式

HRID 1086193 の反応式
Br[CH2:2][CH2:3][CH3:4].[Mg].[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:17])[CH3:16])=[CH:10][CH:9]=1)=[O:7].[Cl-].[NH4+]>O1CCCC1>[OH:7][CH:6]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:17])[CH3:16])=[CH:12][CH:13]=1)[CH2:2][CH2:3][CH3:4]

参加物

6

反応物 4

HCID 78401-BromopropaneHCID 25517Ammonium ChlorideHCID 739424-AcetamidobenzaldehydeHCID 5462224Magnesium

生成物 1

HCID 19875865N-[4-(1-hydroxybutyl)phenyl]acetamide収率 64.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred and refluxed Grignard complex previously prepared starting from 55.1 parts of 1-bromopropane, 10.9 parts of magnesium and tetrahydrofuran was added a solution of 25 parts of N-(4-formylphenyl)acetamide in 225 parts of dry tetrahydrofuran. After stirring for 1 hour at room temperature, the reaction mixture was poured into ice water and a saturated ammonium chloride solution. The organic layer was decanted (and set aside) and the remaining phase was extracted with ethyl acetate. The combined organic layers were dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 20 parts (64.3%) of N-[4-(1-hydroxybutyl)phenyl]acetamide as a residue (interm. 7).

後処理

  1. temperaturerefluxed Grignard complex
  2. custompreviously prepared
  3. stirringAfter stirring for 1 hour at room temperature
  4. customThe organic layer was decanted (and
  5. extractionwas extracted with ethyl acetate
  6. customThe combined organic layers were dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated

出典と根拠

ORDレコード
ord-de9ef7258add4df0810482dbc58bd07b
出典データセット
uspto-grants-1991_07
特許番号
US05028606

反応ノート

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