Water → (3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-yl)-methanol

HRID 402375Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[N:10][N:9]([CH2:12][Si](C)(C)C)[C:8]=1[CH2:17][OH:18].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:12][N:9]1[C:8]([CH2:17][OH:18])=[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[N:11]=[N:10]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (5-pyridin-2-yl-3-trimethylsilanylmethyl-3H-[1,2,3]triazol-4-yl)-methanol (364 mg, 1.39 mmol) in THF (23 mL) was added water (50 μL, 2.78 mmol) and then tetrabutylammonium fluoride (1 M in THF, 1.66 mL, 1.66 mmol) added dropwise at 0° C. The reaction mixture was stirred at 0° C. for 15 min. The resulting mixture was poured into water and then the THF was evaporated. The aqueous layer was then extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 100% ethyl acetate in heptane) afforded the title compound (161 mg, 61%) as an off white solid. MS: m/e=191.2 [M+H]+.

Workup

customthe THF was evaporated
extractionThe aqueous layer was then extracted with ethyl acetate
washthe combined organic extracts washed with brine
dry with materialdried over sodium sulphate
filtrationfiltered
customevaporated
customPurification by chromatography (silica, 0 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-63322169809242d18228438fd3c31062
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08742097B2

Reaction notes

Loading…