Triethylamine → 5-Bromo-2-(tert-butyldimethylsilyloxymethyl)-3-methylpyridine

HRID 42170Notes

Reaction equation

HRID 42170 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([CH2:8][OH:9])=[N:6][CH:7]=1.C(N(CC)CC)C.[C:18]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])([CH3:20])[CH3:19]>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([CH2:8][O:9][Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:24])[CH3:23])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 18329380(5-Bromo-3-methylpyridin-2-YL)methanol

Product 1

HCID 670830095-Bromo-2-(tert-butyldimethylsilyloxymethyl)-3-methylpyridineYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromo-2-hydroxymethyl-3-methylpyridine (1 g, 5 mmol) in N,N-dimethylformamide (50 mL) was added triethylamine (1.56 mL, 15 mmol) and tert-butylchlorodimethylsilane (1.13 g, 7.5 mmol). The mixture was stirred at room temperature for 4 hours, diluted with water (50 mL) and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to give the title compound as a colorless oil (1.51 g, yield 100%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-00c517a72a4342909c551269e58bd53b
Source dataset
uspto-grants-2013_09
Patent number
US08536176B2

Reaction notes

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