Reaction #1365711

Reaction equation

Bis(trimethylsilyl)chloromethane

sodium acrylate

phenothiazine

→

desired product

Bis(trimethylsilyl)methylacrylate

Solvents

butyronitrile

—

hexanes

Conditions

Workup

1. 1
   Otherequipped with a condenser, mechanical stirrer and a nitrogen inlet
2. 2
   Temperatureheated
3. 3
   Temperatureto reflux
4. 4
   Filtrationfiltered
5. 5
   Otherto remove the solids
6. 6
   OtherThe solvents were removed under reduced pressure
7. 7
   workup.DISTILLATIONFractional distillation of the residue under reduced pressure

Procedure

Bis(trimethylsilyl)chloromethane (Aldrich) 39 g, 0.2 mole), sodium acrylate (28 g, 0.3 mole), Adogen 464 (Aldrich) (6.96 g), and phenothiazine (0.10 grams) were placed in a round bottom flask equipped with a condenser, mechanical stirrer and a nitrogen inlet. The flask was charged with 100 ml of butyronitrile and heated to reflux while stirring. After 6 hours, the mixture was diluted with 150 ml hexanes and filtered to remove the solids. The solvents were removed under reduced pressure. Fractional distillation of the residue under reduced pressure gave 35.5 grams 975%) of the desired product at 45-58° C. at 0.5 mm pressure.

Source