Antipyrine → HCID 16063556、化合物

HRID 1993931

反応式

HRID 1993931 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 16063556HCID 16063556、化合物

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

反応条件

温度
40 °C

実験手順

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]+).

後処理

  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

出典と根拠

ORDレコード
ord-a4a5ffe3ebf14fd4bded5c7d451ec43b
出典データセット
uspto-grants-2010_01
特許番号
US07652057B2

関連ノート

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