Imidazole → 5-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-2-methylpyridine

HRID 1590093Notes

Reaction equation

HRID 1590093 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.N1C=CN=C1.[Si:14](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[Si:14]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1)([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 142752-Methyl-5-hydroxypyridineHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 190237195-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-2-methylpyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 10.9 g 5-hydroxypicoline, 8.85 g imidazole and 29.9 mL of t-butyldiphenylsilylchloride in 500 mL of CH2Cl2 was stirred for 4 days at 25° C. The mixture was washed with H2O, brine, dried over MgSO4 and concentrated under vacuum. The crude product was purified by silica gel chromatography (EtOAc/Hexane 10:90) to afford the pure title compound as an oil.

Workup

  1. washThe mixture was washed with H2O, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under vacuum
  4. customThe crude product was purified by silica gel chromatography (EtOAc/Hexane 10:90)

Sources & evidence

ORD record
ord-8c77891e03f94b5898c038b77eb4bf57
Source dataset
uspto-grants-1993_04
Patent number
US05202321

Reaction notes

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