Imidazole → 4-(Tert-butyldimethylsilyloxymethyl)pyridine

HRID 1710685Notes

Reaction equation

HRID 1710685 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.[Si:9](Cl)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].N1C=CN=C1>CN(C=O)C>[Si:9]([O:8][CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 114724-HydroxymethylpyridineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 109878804-(Tert-butyldimethylsilyloxymethyl)pyridineYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of pyridin-4-ylmethanol (8.0 g, 73 mmol), tert-butyldimethylsilyl chloride (14.3 g, 95 mmol) and imidazole (12.9 g, 0.19 mol) in DMF (40 mL) was stirred overnight at room temperature. The reaction was poured onto water and extracted twice with ethyl acetate. The combined organic phases were dried (MgSO4) and evaporated under reduced pressure to yield the title compound as yellow oil (7.5 g, 46%).

Workup

  1. additionThe reaction was poured onto water
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-17d1148fe342484b8a43bfa0f623c223
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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