Water → 2-Ethoxy-5-dimethylsilylpyridine

HRID 867397Notes

Reaction equation

HRID 867397 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][N:5]=1)[CH3:2].Cl[SiH:12]([CH3:14])[CH3:13].[Mg].O>O1CCCC1>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([SiH:12]([CH3:14])[CH3:13])=[CH:6][N:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 66108ChlorodimethylsilaneHCID 8172375-Bromo-2-ethoxypyridineHCID 5462224Magnesium

Product 1

HCID 1317157242-Ethoxy-5-dimethylsilylpyridineYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 18.2 g (0.09 mol) of 2-ethoxy-5-bromopyridine (can be obtained from 2,5-dibromopyridine and sodium methanolate in DMSO), 11.4 g (0.12 mol) of chlorodimethylsilane and 50 ml of anhydrous tetrahydrofuran (THF) is added dropwise to 2.4 g (0.10 mol) of magnesium turnings in 10 ml of anhydrous THF, a strongly exothermic reaction occurring. The reaction is completed by refluxing for two hours. The mixture is then poured into water and extracted repeatedly with n-hexane, The extracts are washed with water and saturated sodium chloride solution, dried and evaporated, and the residue is distilled. 7 g (43%) of 2-ethoxy-5-dimethylsilylpyridine are obtained as a colorless oil of boiling point 7=140°-150° C.

Workup

  1. customa strongly exothermic reaction
  2. temperatureby refluxing for two hours
  3. extractionextracted repeatedly with n-hexane
  4. washThe extracts are washed with water and saturated sodium chloride solution
  5. customdried
  6. customevaporated
  7. distillationthe residue is distilled

Sources & evidence

ORD record
ord-bb79b63bca1945fb99b09014ed8b4eab
Source dataset
uspto-grants-1988_10
Patent number
US04775664

Reaction notes

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