Imidazole → 4-(Tert-butyldimethylsilyloxymethyl)pyridine

HRID 1164880Notes

Reaction equation

HRID 1164880 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.Cl[Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1.C(OCC)(=O)C.CCCCCC>CN(C)C=O>[Si:10]([O:8][CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 114724-HydroxymethylpyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 21226206Ethyl acetate hexane

Product 1

HCID 109878804-(Tert-butyldimethylsilyloxymethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 20 g 4-pyridylcarbinol, 28.9 g of chlorotert-butyl-dimethylsilane and 14.4 g imidazole in 200 ml dimethylformamide is stirred 3 hours at room temperature. Product is isolated by extraction into ethyl acetate/hexane (1:1) and washing extract 4 times with 400 ml of water. The solution is filtered through silica gel and concentrated in vacuo to yield 4-(tert-butyl-dimethylsilyloxymethyl)-pyridine.

Workup

  1. washwashing
  2. extractionextract 4 times with 400 ml of water
  3. filtrationThe solution is filtered through silica gel
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-98c3c3b4938c4f169bd920b2ac1baf19
Source dataset
uspto-grants-1990_03
Patent number
US04906621

Reaction notes

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