Water → 1-(4-(trifluoromethoxy)phenyl)-3-(4-vinylphenyl)-1 H-1,2,4-triazole

HRID 573853노트

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HRID 573853 반응식
N1(C2CCCCCCCCCC2)CCCN=CCCCC[CH2:2]1.[F:23][C:24]([F:46])([F:45])[O:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH:36]=[N:35][C:34]([C:37]3[CH:44]=[CH:43][C:40]([CH:41]=O)=[CH:39][CH:38]=3)=[N:33]2)=[CH:28][CH:27]=1.O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[F:23][C:24]([F:46])([F:45])[O:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]2[CH:36]=[N:35][C:34]([C:37]3[CH:44]=[CH:43][C:40]([CH:41]=[CH2:2])=[CH:39][CH:38]=3)=[N:33]2)=[CH:28][CH:27]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 578244624-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzaldehydeHCID 1296629601,8-Diazabicycloundec-7ene

생성물 1

HCID 904049191-(4-(trifluoromethoxy)phenyl)-3-(4-vinylphenyl)-1 H-1,2,4-triazole수율 69.8%

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 8028Tetrahydrofuran용매

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온도
65 °C

실험 절차

Methyltriphenylphosphonium bromide (32.2 g, 90.0 mmol) and 1,8-diazabicycloundec-7-ene (14.9 mL, 99.0 mmol) were dissolved in tetrahydrofuran (260 mL) and refluxed for 30 minutes. 4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzaldehyde (15.0 g, 45.0 mmol) was added, and the reaction was heated at 65° C. for 5 hours. The solution was cooled and stirred at room temperature overnight. The reaction mixture was poured into water and extracted with hexanes. The organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated. The crude compound was purified by flash column chromatography using 0-70% ethyl acetate/hexanes as eluent to afford the title compound as a white solid (10.4 g, 67%): 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.16 (d, J=8.3 Hz, 2H), 7.80 (d, J=9.0 Hz, 2H), 7.58-7.47 (m, 2H), 7.39 (d, J=9.1 Hz, 2H), 6.77 (dd, J=17.6, 10.9 Hz, 1H), 5.84 (dd, J=17.6, 0.8 Hz, 1H), 5.32 (dd, J=10.9, 0.8 Hz, 1H); 19F NMR (376 MHz, CDCl3) δ −58.02; ESIMS m/z 332 ([M+H]+).

후처리

  1. temperaturerefluxed for 30 minutes
  2. temperatureThe solution was cooled
  3. extractionextracted with hexanes
  4. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude compound was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-77b16e376ed34fab8d4257bc8e78fa50
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029560B2

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