m-Chloroperbenzoic acid → 3-(4-(7-oxabicyclo[4.1.0]heptan-1-yl)phenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole

HRID 573931

反応式

HRID 573931 の反応式
[C:1]1([C:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH:28]=2)[CH:6]=[CH:5][C:4]([C:7]2[N:11]=[CH:10][N:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)[N:8]=2)=[CH:3][CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:34]>C(OCC)C>[C:23]12([C:1]3[CH:2]=[CH:3][C:4]([C:7]4[N:11]=[CH:10][N:9]([C:12]5[CH:13]=[CH:14][C:15]([O:18][C:19]([F:20])([F:21])[F:22])=[CH:16][CH:17]=5)[N:8]=4)=[CH:5][CH:6]=3)[O:34][CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28]2

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 904116523-(2',3',4',5'-tetrahydro-[1,1'-biphenyl]-4-yl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole

生成物 1

HCID 904128703-(4-(7-oxabicyclo[4.1.0]heptan-1-yl)phenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole収率 77.2%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

To a solution of 3-(2′,3′,4′,5′-tetrahydro-[1,1′-biphenyl]-4-yl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (CB10) (3.11 g, 8.07 mmol) in diethyl ether (60 mL) was added meta-chloroperoxybenzoic acid (70%; 2.79 g, 11.3 mmol) slowly at 0° C. The reaction was stirred and allowed to gradually warm to room temperature, then stirring was continued for 18 hours. The solution was diluted in diethyl ether, washed with sodium bicarbonate, extracted with diethyl ether, washed with water, and extracted again with diethyl ether. The organics were dried, filtered, and concentrated providing the title compound as a white solid (2.5 g, 77%) which was used without further purification: 1H NMR (400 MHz, CDCl3) δ 8.58 (s, 1H), 8.20-8.11 (m, 2H), 7.84-7.77 (m, 2H), 7.52-7.46 (m, 2H), 7.39 (dt, J=8.0, 1.0 Hz, 2H), 3.12 (dd, J=3.1, 1.7 Hz, 1H), 2.34 (ddd, J=14.9, 8.5, 5.3 Hz, 1H), 2.09-1.95 (m, 2H), 1.74-1.45 (m, 4H), 1.42-1.28 (m, 1H); 19F NMR (376 MHz, CDCl3) δ −58.03; ESIMS m/z 402 ([M+H]+).

後処理

  1. stirringstirring
  2. washwashed with sodium bicarbonate
  3. extractionextracted with diethyl ether
  4. washwashed with water
  5. extractionextracted again with diethyl ether
  6. customThe organics were dried
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-3f454e95a99a42078b09e26d392358a6
出典データセット
uspto-grants-2015_05
特許番号
US09029560B2

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