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

HRID 1772454ノート

反応式

HRID 1772454 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

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]+).

後処理

  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

出典と根拠

ORDレコード
ord-f777e2ad41f14a1aa1cf6b6e6bb87f5a
出典データセット
uspto-grants-2016_02
特許番号
US09249133B2

反応ノート

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