Sodium hydride → HCID 178455036, compound

HRID 2168441Notes

Reaction equation

HRID 2168441 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([OH:10])[C:4]=2[N:3]=[N:2]1.[H-].[Na+].[C:13]([Si:17](Cl)([CH3:19])[CH3:18])([CH3:16])([CH3:15])[CH3:14]>O1CCCC1>[Si:17]([O:10][C:9]1[C:4]2[N:3]=[N:2][NH:1][C:5]=2[CH:6]=[CH:7][CH:8]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 178455036HCID 178455036, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1H-benzo[d][1,2,3]triazol-4-ol (2.0 g) in tetrahydrofuran (30 mL) was treated with 60% sodium hydride (0.622 g). After 10 minutes, tert-butylchlorodimethylsilane (2.454 g) was added. The solution was stirred for 16 hours. The solvent was removed, and the residue was purified by flash column chromatography on silica gel using 10-50% ethyl acetate in hexanes as eluent to give the title compound.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by flash column chromatography on silica gel using 10-50% ethyl acetate in hexanes as eluent

Sources & evidence

ORD record
ord-ab4e739cc8d04d06b54591f73c685a57
Source dataset
uspto-grants-2015_06
Patent number
US09045420B2

Reaction notes

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