Sodium hydride → HCID 86724053, compound

HRID 1519132Notes

Reaction equation

HRID 1519132 reaction equation
[N+:1]([C:4]1[N:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[H-].[Na+].Cl[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[N+:1]([C:4]1[CH:8]=[N:7][N:6]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[N:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178526868HCID 178526868, compound

Product 1

HCID 86724053HCID 86724053, compoundYield 57.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-nitro-1H-triazole (5.00 g, 43.84 mmol) in THF (230 mL), cooled to 0° C., was added sodium hydride (2.28 g, 56.99 mmol) portionwise over 30 min. The mixture was stirred for a further 30 min and then 2-(chloromethoxy)ethyl-trimethyl-silane (7.67 g, 8.15 mL, 46.03 mmol) was added dropwise. The reaction was allowed to warm to room temperature and stirred for 2 h, then re-cooled to 0° C. and quenched with water. The mixture was extracted with EtOAc and the organics washed with brine, dried (MgSO4) and concentrated. The residue was purified by column chromatography eluting with 5% EtOAc in hexanes to afford 4-nitro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-1,2,3-triazole (6.18 g, 56%) and 4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,3-triazole as an off white solid (3.52 g, 33%).

Workup

  1. stirringstirred for 2 h
  2. temperaturere-cooled to 0° C.
  3. customquenched with water
  4. extractionThe mixture was extracted with EtOAc
  5. washthe organics washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography
  9. washeluting with 5% EtOAc in hexanes

Sources & evidence

ORD record
ord-4a061bd57a2b4ac4bd0839c66cc1e1e4
Source dataset
uspto-grants-2015_07
Patent number
US09073875B2

Reaction notes

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