Water → HCID 57746172, compound

HRID 2365236Notes

Reaction equation

HRID 2365236 reaction equation
C[Si]([CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:8]=[N:7]1)(C)C.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:8]=[N:7]1

Participants

5

Reactant 3

HCID 962Water2×HCID 2724141Tetrabutylammonium FluorideHCID 67495995HCID 67495995, compound

Product 1

HCID 57746172HCID 57746172, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(1-trimethylsilanylmethyl-1H-[1,2,3]triazol-4-yl)-pyridine (6.05 g, 26 mmol) in THF (435 mL) was added water (0.94 mL, 52 mmol) and then tetrabutylammonium fluoride (1 M in THF, 31.2 mL, 31 mmol) was added dropwise at 0° C. The reaction mixture was stirred at 0° C. for 1 h. 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 (3.53 g, 85%) as a light brown solid. MS: m/e=161.2 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-474370794d3b41b983f9703b0f1bead7
Source dataset
uspto-grants-2014_04
Patent number
US08697696B2

Reaction notes

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