Triethylamine → 1-(4'-Fluorophenyl)-1,3-DihydroIsobenzofuran-5-Carbonitrile

HRID 585343ノート

反応式

HRID 585343 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]=O)=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1.Cl.NO.C([N:24](CC)CC)C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]#[N:24])=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 102204271-(4'-Fluorophenyl)-1,3-dihydroisobenzofuran-5-carbaldehyde

生成物 1

HCID 98561591-(4'-Fluorophenyl)-1,3-DihydroIsobenzofuran-5-Carbonitrile収率 59.8%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

1-(4′-Fluorophenyl)-1,3-dihydroisobenzofuran-5-carbaldehyde (17.00 g) was dissolved in toluene (200 ml) and hydroxylamine hydrochloride (5.5 g) and triethylamine (8.0 g) were added. The mixture was stirred at 80-100° C. for 2 hr. The obtained triethylamine hydrochloride was filtered and the solvent was evaporated. Thereto was added acetic anhydride (36.5 g) and the mixture was stirred at 125-130° C. for 5 hr. The reaction mixture was poured into 10% aqueous sodium hydroxide solution (300 ml) and extracted twice with toluene (200 ml). The toluene layer was washed successively with 5% aqueous sodium hydroxide solution, water and saturated brine and dried over magnesium sulfate. Silica gel (5 g) was added and the mixture was thoroughly stirred and filtered. The solvent was evaporated to give crude 1-(4′-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (14.2 g). This was recrystallized from a mixed solvent of ethanol/hexane to give 1-(4′-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (9.52 g, 59.8%).

後処理

  1. filtrationThe obtained triethylamine hydrochloride was filtered
  2. customthe solvent was evaporated
  3. additionThereto was added acetic anhydride (36.5 g)
  4. stirringthe mixture was stirred at 125-130° C. for 5 hr
  5. additionThe reaction mixture was poured into 10% aqueous sodium hydroxide solution (300 ml)
  6. extractionextracted twice with toluene (200 ml)
  7. washThe toluene layer was washed successively with 5% aqueous sodium hydroxide solution, water and saturated brine
  8. dry with materialdried over magnesium sulfate
  9. additionSilica gel (5 g) was added
  10. stirringthe mixture was thoroughly stirred
  11. filtrationfiltered
  12. customThe solvent was evaporated
  13. customto give crude 1-(4′-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile (14.2 g)
  14. customThis was recrystallized from a mixed solvent of ethanol/hexane

出典と根拠

ORDレコード
ord-63d0530ac7cc4c448f03cbbdcf0dfd27
出典データセット
uspto-grants-2005_08
特許番号
US06930211B2

反応ノート

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