Aluminium lithium hydride → 1-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-carbaldehyde

HRID 2090936노트

반응식

HRID 2090936 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[C:11]([C:13](OC)=[O:14])[C:10]([CH3:17])=[N:9]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[C:11]([CH:13]=[O:14])[C:10]([CH3:17])=[N:9]1

참가 물질

6

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 66777678HCID 66777678, 화합물2회

생성물 1

HCID 433815061-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-carbaldehyde수율 15.3%

시약·촉매·용매 3

HCID 178418406HCID 178418406, 화합물촉매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution (20 mL) of methyl 1-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-carboxylate (2.0 g) synthesized in the above-mentioned (1) in tetrahydrofuran was added to an ice-cooled solution (20 mL) of lithium aluminum hydride (0.30 g) in tetrahydrofuran. The ice bath was removed, and the reaction mixture was stirred at room temperature for 1 hr. The mixture was ice-cooled again, and water (0.80 mL), 1N aqueous sodium hydroxide solution (4.0 mL) and water (0.80 mL) were successively added dropwise to quench the reaction. The residue was filtered through celite, and the filtrate was concentrated under reduced pressure to give a crude product (0.36 g) of 1-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-methanol as a pale-yellow oil. This was dissolved in toluene (10 mL), manganese dioxide (2.0 g) was added, and the mixture was heated under reflux with a Dean-Stark trap for 1 hr. The reaction mixture was allowed to cool to room temperature, and manganese dioxide was collected by filtration. The solvent was evaporated under reduced pressure to give the title object compound (0.27 g, 15%) as a colorless solid.

후처리

  1. customThe ice bath was removed
  2. temperaturecooled again
  3. additionwater (0.80 mL), 1N aqueous sodium hydroxide solution (4.0 mL) and water (0.80 mL) were successively added dropwise
  4. customto quench
  5. customthe reaction
  6. filtrationThe residue was filtered through celite
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customto give a crude product (0.36 g) of 1-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-methanol as a pale-yellow oil
  9. temperaturethe mixture was heated
  10. temperatureunder reflux with a Dean-Stark trap for 1 hr
  11. temperatureto cool to room temperature
  12. filtrationmanganese dioxide was collected by filtration
  13. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-97bedd54db654e0483e48f9ed2e73b54
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436043B2

반응 노트

불러오는 중…