Tetrahydrofuran → cyclopropyl(1-(4-vinylphenyl)-1H-1,2,4-triazol-5-yl)methanone

HRID 587283Notes

Reaction equation

HRID 587283 reaction equation
[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]CCCC.[CH2:19]1[CH2:23][O:22][CH2:21][CH2:20]1>>[CH:19]1([C:23]([C:13]2[N:9]([C:6]3[CH:5]=[CH:4][C:3]([CH:1]=[CH2:2])=[CH:8][CH:7]=3)[N:10]=[CH:11][N:12]=2)=[O:22])[CH2:20][CH2:21]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 585499641-(4-vinylphenyl)-1H-1,2,4-triazoleHCID 178418339Butyllithium

Product 1

HCID 86675220cyclopropyl(1-(4-vinylphenyl)-1H-1,2,4-triazol-5-yl)methanone

Procedure

To a stirred solution of 1-(4-vinyl-phenyl)-1H-[1,2,4]triazole (1 g, 5.8 mmol) in 25 mL of THF, was added n-BuLi (0.37 g, 5.8 mmol) at −78° C. and stirred for 30 min To this N-methoxy N-methylcyclopropoxide in THF (0.82 g, 6.4 mmol) was added and the resultant reaction mixture was stirred at ambient temperature 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) to afford the title compound as an off white solid (420 mg, 30%): mp 90-91° C.; 1H NMR (400 MHz, CDCl3) δ 8.12 (s, 1H), 7.50 (d, J=7.8 Hz, 2H), 7.38 (d, J=7.8 Hz, 2H), 6.75 (dd, J=16.3, 10.7 Hz, 1H), 5.81 (d, J=16.3 Hz, 1H), 5.35 (d, J=10.7 Hz, 1H), 3.22 (m, 1H), 1.27 (m, 2H), 1.18 (m, 2H); ESIMS m/z 240.18 ([M+H]+); IR (thin film) 2922, 1630 cm−1.

Workup

  1. additionwas added
  2. customthe resultant reaction mixture
  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
  8. customThe crude compound was purified by flash chromatography (SiO2, 100-200 mesh, 40% EtOAc in Pet ether)

Sources & evidence

ORD record
ord-f46c69a2431147bca300fec26b8245f5
Source dataset
uspto-grants-2016_01
Patent number
US09226500B2

Reaction notes

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