Ammonium Chloride → 1-(1-Methyl-1H-pyrazol-5-yl)-3-[4-(trifluoromethyl)phenyl]prop-2-yn-1-one

HRID 238377

反応式

HRID 238377 の反応式
C[Mg]Br.[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)#[CH:5].CON(C)[C:19]([C:21]1[N:25]([CH3:26])[N:24]=[CH:23][CH:22]=1)=[O:20].[Cl-].[NH4+]>O1CCCC1>[CH3:26][N:25]1[C:21]([C:19](=[O:20])[C:5]#[C:4][C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:13])([F:14])[F:15])=[CH:8][CH:7]=2)=[CH:22][CH:23]=[N:24]1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 43482951-Ethynyl-4-(trifluoromethyl)benzeneHCID 62038410N-methoxy-N,1-dimethyl-1H-pyrazole-5-carboxamideHCID 178418573HCID 178418573、化合物

生成物 1

HCID 866848751-(1-Methyl-1H-pyrazol-5-yl)-3-[4-(trifluoromethyl)phenyl]prop-2-yn-1-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

Methyl magnesium bromide (9.70 mL, 1.0 M tetrahydrofuran solution) was added dropwise to a tetrahydrofuran (4.0 mL) solution of 1-ethynyl-4-(trifluoromethyl)benzene (1.80 mL) under cooling in an ice bath, and the obtained solution was then stirred for 2 hours. Thereafter, the reaction solution was cooled to −78° C., and a tetrahydrofuran (6.2 mL) solution of N-methoxy-N,1-dimethyl-1H-pyrazol-5-carboxamide (867 mg) was then added thereto. The obtained mixture was stirred for 1 hour, and was then stirred for 2.5 hours under cooling in an ice bath. Thereafter, a saturated ammonium chloride aqueous solution was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was washed with a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=9:1), so as to obtain the title compound (1.09 g) in the form of a yellow oily substance.

後処理

  1. temperatureunder cooling in an ice bath
  2. stirringThe obtained mixture was stirred for 1 hour
  3. stirringwas then stirred for 2.5 hours
  4. temperatureunder cooling in an ice bath
  5. extractionthe obtained mixture was then extracted with ethyl acetate
  6. washThe organic layer was washed with a saturated saline
  7. dry with materialwas then dried over anhydrous magnesium sulfate
  8. concentrationfollowed by vacuum concentration
  9. customThe residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=9:1)

出典と根拠

ORDレコード
ord-1e143a062e8842108de2bd636e760884
出典データセット
uspto-grants-2014_02
特許番号
US08642626B2

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