Propargyl alcohol → 3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)prop-2-yn-1-ol

HRID 62062

반응식

HRID 62062 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[CH:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[CH2:24]([OH:27])[C:25]#[CH:26]>C(N(CC)CC)C.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:21][C:20]([F:23])([F:22])[O:19][C:16]1[CH:17]=[CH:18][C:13]([N:10]2[CH:11]=[N:12][C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:26]#[C:25][CH2:24][OH:27])=[CH:3][CH:4]=3)=[N:9]2)=[CH:14][CH:15]=1

참가 물질

8

반응물 2

HCID 7859Propargyl alcoholHCID 904040773-(4-bromophenyl)-1-(4-(trifluoromethoxy)phenyl)-1 H-1,2,4-triazole

생성물 1

HCID 1186751543-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)prop-2-yn-1-ol수율 34.1%

시약·촉매·용매 5

HCID 11776Triphenylphosphine촉매HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

In a 1000 mL flask, 3-(4-bromophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (25.0 g, 65.3 mmol) and propargyl alcohol (4.4 g, 78.36 mmol) were diluted with triethylamine (250 mL). Then bis(triphenylphosphine)palladium(II) chloride (0.915 g, 0.0200 mmol), copper(I) iodide (0.320 g, 0.169 mmol) and triphenylphosphine (0.102 g, 0.150 mmol) were added. The reaction was heated to 70° C. and stirred for 16 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and filtered through Celite®. A Brine solution was added to the filtrate and stirred for 15 minutes. The layers were separated and the aqueous layer further extracted with ethyl acetate. The combined organics were dried over magnesium sulfate, filtered, and concentrated. The resulting residue was purified by flash column chromatography using 15% ethyl acetate/petroleum ether as eluent to afford the title compound as yellow solid (8.00 g, 33%): mp 110-113° C.; 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1H), 8.15 (d, J=8.4 Hz, 2H), 7.80 (d, J=9.0 Hz, 2H), 7.54 (d, J=8.4 Hz, 2H), 7.39 (d J=8.4, 2H), 4.53 (d, J=4.8, 2H), 1.80-1.74 (brs, 1H); ES+API m/z 360 ([M+H]+).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through Celite®
  3. additionA Brine solution was added to the filtrate
  4. stirringstirred for 15 minutes
  5. customThe layers were separated
  6. extractionthe aqueous layer further extracted with ethyl acetate
  7. dry with materialThe combined organics were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting residue was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-d9a9ffac728f45d18c3f04c2ed18ee4e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09445594B2

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