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

HRID 585343노트

반응식

HRID 585343 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-63d0530ac7cc4c448f03cbbdcf0dfd27
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06930211B2

반응 노트

불러오는 중…