Imidazole → 4-(Tert-butyldimethylsilyloxymethyl)pyridine

HRID 2202587Notes

Reaction equation

HRID 2202587 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.O>CN(C)C=O>[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

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 114724-HydroxymethylpyridineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 109878804-(Tert-butyldimethylsilyloxymethyl)pyridineYield 100.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Pyridin-4-ylmethanol (2.2 g, 20 mmol) was dissolved in N,N-dimethylformamide, and tert-butyldimethylsilyl chloride (3.3 g, 22 mmol) and imidazole (2.0 g, 30 mmol were added thereto. The mixture was stirred at a room temperature overnight. After the completion of the reaction was confirmed by HPLC, water was added to the mixture, and the extraction with diethyl ether was performed 3 times. The combined organic layer was washed with a saturated saline solution and dried over magnesium sulfate, and the solvent was distilled off. Thus the title compound (4.5 g, 100%) was obtained as an oily substance.

Workup

  1. additionwas added to the mixture
  2. extractionthe extraction with diethyl ether
  3. washThe combined organic layer was washed with a saturated saline solution
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-388117f89be84b56a391f5f7b375ac7a
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

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