Antipyrine → HCID 16063556, 화합물

HRID 1993931

반응식

HRID 1993931 반응식
[C:1](O)([CH3:4])([CH3:3])[CH3:2].[CH3:6][N:7]1[C:11]([CH3:12])=[CH:10][C:9](=[O:13])[N:8]1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.B(F)(F)F.[OH-].[Na+]>ClC(Cl)C>[C:1]([C:10]1[C:9](=[O:13])[N:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:7]([CH3:6])[C:11]=1[CH3:12])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 2206AntipyrineHCID 6356Boron trifluorideHCID 6386tert-ButanolHCID 14798Sodium Hydroxide

생성물 1

HCID 16063556HCID 16063556, 화합물

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

반응 조건

온도
40 °C

실험 절차

To a solution tert-butanol (800 μL) and 1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (0.150 g) in dichloroethane (1 mL) was added boron trifluoride diethyletherate (400 μL). The reaction was heated to 40° C. over seven days. The reaction mixture was then cooled and poured onto an ice/water mixture, was basified to pH 10 using sodium hydroxide solution and was extracted with EtOAc. The solution was acidified with AcOH to pH=4 and further extracted with EtOAc. The combined organic phases were washed with brine and dried over sodium sulfate. Filtration and evaporation of the volatiles in vacuo afforded a crude residue which was purified via flash column chromatography to afford 4-tert-butyl-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (0.025 mg) as a white solid. MS (ESI+): 245.4 [M+H]+).

후처리

  1. temperatureThe reaction mixture was then cooled
  2. extractionwas extracted with EtOAc
  3. extractionfurther extracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationFiltration and evaporation of the volatiles in vacuo
  7. customafforded a crude residue which
  8. customwas purified via flash column chromatography

출처 및 근거

ORD 기록
ord-a4a5ffe3ebf14fd4bded5c7d451ec43b
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652057B2

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