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

HRID 587750노트

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HRID 587750 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 312751,4-Dioxane용매

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온도
70 °C

실험 절차

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]+).

후처리

  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)

출처 및 근거

ORD 기록
ord-fd95f865b7fb4e278a1e5c8da2c10651
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09226501B2

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