Pyridine → 2-((Trimethylsilyl)oxy)ethyl methacrylate

HRID 1583270Notes

Reaction equation

HRID 1583270 reaction equation
[C:1]([O:6][CH2:7][CH2:8][OH:9])(=[O:5])[C:2]([CH3:4])=[CH2:3].N1C=CC=CC=1.[CH3:16][Si:17]([CH3:20])([CH3:19])Cl>C(Cl)(Cl)(Cl)Cl>[C:1]([O:6][CH2:7][CH2:8][O:9][Si:17]([CH3:20])([CH3:19])[CH3:16])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6397ChlorotrimethylsilaneHCID 133602-Hydroxyethyl Methacrylate

Product 1

HCID 870942-((Trimethylsilyl)oxy)ethyl methacrylateYield 91.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In a three-neck flask having a capacity of 500 ml, 26 g (0.2 moles) of 2-hydroxyethyl methacrylate (abbreviated to HEMA) and 16 g of pyridine were dissolved in 200 ml of carbon tetrachloride. At room temperature, 107.5 g (0.2 moles) of trimethylchlorosilane was slowly dropped into the solution in the flask to complete the addition of the entire amount in 30 min. During this process precipitation of hydrochloric acid salt of pyridine took place. After filtration, carbon tetrachloride in the reaction liquid was distilled out by using an evaporater, and the remaining liquid was distilled under reduced pressure to obtain 37 g of 2-trimethylsiloxyethyl methacrylate (abbreviated to HEMA-Si).

Workup

  1. customIn a three-neck flask having
  2. additionthe addition of the entire amount in 30 min
  3. customDuring this process precipitation of hydrochloric acid salt of pyridine
  4. filtrationAfter filtration, carbon tetrachloride
  5. customin the reaction liquid
  6. distillationwas distilled out
  7. distillationthe remaining liquid was distilled under reduced pressure

Sources & evidence

ORD record
ord-de3eda4fa03446058f88cb87e3d05a3b
Source dataset
uspto-grants-1985_11
Patent number
US04551417

Reaction notes

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