Ammonium Chloride → 1-(3,4-dichlorophenyl)-6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-ol

HRID 71153ノート

反応式

HRID 71153 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([C:25]#[C:26][CH2:27][CH2:28][CH2:29][CH:30]=[O:31])[CH:16]=[CH:17][C:18]=1[N:19]1[CH:23]=[N:22][C:21]([CH3:24])=[N:20]1.[Cl-].[NH4+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]([OH:31])[CH2:29][CH2:28][CH2:27][C:26]#[C:25][C:15]2[CH:16]=[CH:17][C:18]([N:19]3[CH:23]=[N:22][C:21]([CH3:24])=[N:20]3)=[C:13]([O:12][CH3:11])[CH:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 866629766-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-ynalHCID 178478192HCID 178478192、化合物2 回

生成物 1

HCID 666089951-(3,4-dichlorophenyl)-6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3,4-Dichlorophenylmagnesium bromide (0.5 M THF solution, 13 mL) was added dropwise to a mixture of 6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-ynal (900 mg) in THF (32 mL) at −78° C., and the mixture was stirred for 1 hr under ice-cooling and at room temperature for 14 hr. 3,4-Dichlorophenylmagnesium bromide (0.5M THF solution, 13 mL) was added to the reaction mixture under ice-cooling, and the mixture was stirred for 1 hr under ice-cooling. Saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (349 mg).

後処理

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1 hr under ice-
  3. temperaturecooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-fdd22228dd8b44e684b3e9880bb56cfe
出典データセット
uspto-grants-2014_09
特許番号
US08822699B2

反応ノート

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