Methyl iodide → 4-(methoxymethyl)-5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole

HRID 623705Notes

Reaction equation

[F:1][C:2]([F:29])([F:28])[O:3][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[O:7][C:8]1[C:9]([CH2:23][OH:24])=[N:10][N:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[N:12]=1.[H-].[Na+].I[CH3:33]>O1CCCC1.O>[CH3:33][O:24][CH2:23][C:9]1[C:8]([O:7][C:6]2[CH:25]=[CH:26][CH:27]=[C:4]([O:3][C:2]([F:1])([F:28])[F:29])[CH:5]=2)=[N:12][N:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:21])([F:22])[F:20])=[CH:15][CH:14]=2)[N:10]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a stirred solution of 5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole-4-methanol (i.e. the product of Example 5, Step I, 0.075 g, 0.18 mmol) in anhydrous tetrahydrofuran (2 mL) was added sodium hydride (0.011 g, 0.28 mmol, 60% dispersion in oil). After 15 min., iodomethane (0.017 mL, 0.27 mmol) was added. The mixture was stirred at 23° C. for 1.75 h. The reaction mixture was diluted with water (20 mL), extracted with diethyl ether (3×15 mL), and washed with saturated aqueous sodium chloride solution (10 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford the crude product which was purified by chromatography on silica gel eluting with 0 to 10% ethyl acetate in hexanes to obtain the title compound (0.045 g.) as a clear, colorless oil.

Workup

extractionextracted with diethyl ether (3×15 mL)
washwashed with saturated aqueous sodium chloride solution (10 mL)
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated under reduced pressure
customto afford the crude product which
customwas purified by chromatography on silica gel eluting with 0 to 10% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-0dd85bb7ba0c4936b9480c4d4dd34f9a
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09302999B2

Reaction notes

Loading…