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

HRID 1503767ノート

反応式

HRID 1503767 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4f5e8679bd6d432e96f68f4147afc4b7
出典データセット
uspto-grants-2015_12
特許番号
US09212164B2

反応ノート

読み込み中…