Potassium Carbonate → 1-(4-vinylphenyl)-1H-1,2,4-triazole

HRID 587750ノート

反応式

HRID 587750 の反応式
[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.[C:14]([O-])([O-])=O.[K+].[K+]>O1CCOCC1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:10]([C:9]1[CH:12]=[CH:13][C:6]([N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)=[CH:7][CH:8]=1)=[CH2:14]

参加物

5

反応物 2

HCID 11430Potassium CarbonateHCID 27764884-(1H-1,2,4-triazol-1-yl)benzaldehyde

生成物 1

HCID 585499641-(4-vinylphenyl)-1H-1,2,4-triazole収率 63%

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
70 °C

実験手順

To a stirred solution of 4-[1,2,4]-triazol-1-yl-benzaldehyde (9.0 g, 52 mmol) in 1,4-dioxane (100 mL), were added K2CO3 (10.76 g, 78 mmol) and methyl triphenyl phosphonium bromide (22.2 g, 62.4 mmol) at room temperature. The resultant reaction mixture was heated to 70° C. for 18 h. After completion of the reaction (TLC), the reaction mixture was cooled to room temperature and filtered and the obtained filtrate was concentrated under reduced pressure. Purification by flash chromatography (SiO2, 100-200 mesh; 25-30% EtOAc in petroleum ether) to afforded the title compound as a white solid (5.6 g, 63%): ESIMS m/z 172.09 ([M+H]+).

後処理

  1. customThe resultant reaction mixture
  2. customAfter completion of the reaction (TLC)
  3. temperaturethe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. concentrationthe obtained filtrate was concentrated under reduced pressure
  6. customPurification by flash chromatography (SiO2, 100-200 mesh; 25-30% EtOAc in petroleum ether)

出典と根拠

ORDレコード
ord-fd95f865b7fb4e278a1e5c8da2c10651
出典データセット
uspto-grants-2016_01
特許番号
US09226501B2

反応ノート

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