Ammonium Chloride → HCID 89586435、化合物

HRID 1747826

反応式

HRID 1747826 の反応式
[C:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=[CH:5][CH:4]=1)#[CH:2].C([Li])CCC.[C:19]1([C:25]#[C:26][CH:27]=[O:28])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+]>C1COCC1>[C:19]1([C:25]#[C:26][CH:27]([OH:28])[C:2]#[C:1][C:3]2[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:6]=[CH:5][CH:4]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 75740PhenylpropynalHCID 895863365-ethynyl-1-phenyl-1H-pyrazoleHCID 178418339Butyllithium

生成物 1

HCID 89586435HCID 89586435、化合物収率 82.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a solution of 5-ethynyl-1-phenyl-1H-pyrazole (0.500 g) in THF (20.0 mL) was added dropwise 2.5M butyllithium in THF solution (1.55 mL) at −78° C., and the mixture was stirred for 30 min. To the reaction mixture was added dropwise a solution of 3-phenylprop-2-ynal (0.464 g) in THF (5.00 mL) at −78° C., the mixture was stirred for 45 min, and saturated aqueous ammonium chloride solution (10.0 mL) was added. The mixture was extracted with dichloromethane, the extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane/methanol) to give the title compound (0.73 g).

後処理

  1. stirringthe mixture was stirred for 45 min
  2. extractionThe mixture was extracted with dichloromethane
  3. washthe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (dichloromethane/methanol)

出典と根拠

ORDレコード
ord-7d57d89db4b845bc934a381b30beb8c2
出典データセット
uspto-grants-2015_10
特許番号
US09150588B2

関連ノート

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