Reaction #1365710

Reaction equation

2-Trimethylsilylethanol

methacryloyl chloride

pyridine

→

desired product

Yield 44.7%

2-Trimethylsilylethylmethacrylate

Yield 44.7%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Otherequipped with a condenser, addition funnel, magnetic stirrer and a nitrogen inlet
2. 2
   OtherA mildly exothermic reaction
3. 3
   workup.STIRRINGThe mixture was stirred overnight at room temperature
4. 4
   WashAfterwards, the mixture was washed with 1×100 ml
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   ConcentrationThe solution was concentrated in vacuo
7. 7
   workup.DISTILLATIONFractional distillation under reduced pressure

Procedure

2-Trimethylsilylethanol (Aldrich) (30 g, 0.25 mole) was placed in a round bottom flask equipped with a condenser, addition funnel, magnetic stirrer and a nitrogen inlet. 200 ml dichloromethane, pyridine (20.80 g, 0.26 mole) and 100 mg of phenothiazine were added to the flask. While stirring, methacryloyl chloride (27.18 g, 0.26 mole) in 100 ml dichloromethane was added dropwise at room temperature. A mildly exothermic reaction occurred. The mixture was stirred overnight at room temperature. Afterwards, the mixture was washed with 1×100 ml deionized water and 2×100 ml brine and dried over anhydrous magnesium sulfate. The solution was concentrated in vacuo. Fractional distillation under reduced pressure gave 20.82 grams of the desired product at 35-38° C. at 0.5 mm.

Source