Methyl iodide → 5-methyl-1-(4-vinylphenyl)-1H-1,2,4-triazole

HRID 1503595노트

반응식

HRID 1503595 반응식
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)=[CH:5][CH:4]=1)=[CH2:2].[Li][CH2:15]CCC.CI>C1COCC1>[CH3:15][C:13]1[N:9]([C:6]2[CH:5]=[CH:4][C:3]([CH:1]=[CH2:2])=[CH:8][CH:7]=2)[N:10]=[CH:11][N:12]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 585499641-(4-vinylphenyl)-1H-1,2,4-triazoleHCID 178418339Butyllithium

생성물 1

HCID 866752225-methyl-1-(4-vinylphenyl)-1H-1,2,4-triazole수율 46.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred solution of 1-(4-vinyl-phenyl)-1H-[1,2,4]triazole (0.5 g, 2.9 mmol) in 10 mL of THF, was added n-BuLi (0.22 g, 3.5 mmol) at −78° C. and stirred for 30 min. To this methyl iodide in THF (0.50 g, 3.5 mmol) was added and the resultant reaction mixture was stirred at RT for 16 h. The reaction mixture was quenched with a saturated aqueous NH4Cl solution and extracted with EtOAc (3×25 mL). The combined EtOAc layer was washed with brine and dried over sodium sulphate and concentrated under reduced pressure The crude compound was purified by flash chromatography (SiO2, 100-200 mesh, 40% EtOAc in Pet ether) afford the title compound as a pale brown liquid (250 mg, 46%): 1H NMR (400 MHz, CDCl3) δ 7.93 (s, 1H), 7.55 (d, J=9 Hz, 2H), 7.42 (d, J=9 Hz, 2H), 6.76 (dd, J=18, 11 Hz, 1H), 5.83 (d, J=18 Hz, 1H), 5.38 (d, J=11 Hz, 1H), 2.55 (s, 3H); ESIMS m/z 186.13 ([M+H]+); IR (thin film) 1517, 1386, 1182, 847 cm−1.

후처리

  1. customthe resultant reaction mixture
  2. stirringwas stirred at RT for 16 h
  3. customThe reaction mixture was quenched with a saturated aqueous NH4Cl solution
  4. extractionextracted with EtOAc (3×25 mL)
  5. washThe combined EtOAc layer was washed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure The crude compound
  8. customwas purified by flash chromatography (SiO2, 100-200 mesh, 40% EtOAc in Pet ether)

출처 및 근거

ORD 기록
ord-1b89dc22b8f84af28442e7c18e13dc0c
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212163B2

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