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

반응식

HRID 573931 반응식
[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

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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]+).

후처리

  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

출처 및 근거

ORD 기록
ord-3f454e95a99a42078b09e26d392358a6
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029560B2

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