Imidazole → HCID 178455171, compound

HRID 708334Notes

Reaction equation

HRID 708334 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][OH:7])[N:3]=[N:2]1.N1C=CN=C1.[CH3:13][C:14]([Si:17](Cl)([CH3:19])[CH3:18])([CH3:16])[CH3:15]>C(Cl)Cl>[Si:17]([O:7][CH2:6][C:4]1[N:3]=[N:2][NH:1][CH:5]=1)([C:14]([CH3:16])([CH3:15])[CH3:13])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 178519888HCID 178519888, compound

Product 1

HCID 178455171HCID 178455171, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1H-1,2,3-triazol-4-yl)methanol (30 g, 200 mmol) in DCM (160 mL) was added imidazole (20.4 g, 300 mmol) followed by TBDMS-Cl (33.3 g, 220 mmol) as a solid in portions. After stirring at rt for 16 h, the reaction mixture was filtered through celite, and the filtrate was concentrated in vacuo. The residue was dissolved in EtOAc (500 mL) and washed with water, brine, dried over Na2SO4, and concentrated in vacuo. The crude residue was purified via silica gel chromatography (EtOAc-hexanes, 5-30%) to afford the title compound (30.2 g, 71%) as a pale yellow solid.

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc (500 mL)
  4. washwashed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified via silica gel chromatography (EtOAc-hexanes, 5-30%)

Sources & evidence

ORD record
ord-c8299b437c0046dc9191396dc91ed770
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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