Reaction #742258

Reaction equation

3-[2-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-acrylic acid tert-butyl-dimethyl-silyl ester

oxalyl chloride

→

3-[2-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-acryloyl chloride

Solvents

CH2Cl2

Conditions

Workup

1. 1
   workup.ADDITIONAfter complete addition the reaction mixture
2. 2
   FiltrationThe reaction mixture was filtered
3. 3
   Otherevaporated to dryness
4. 4
   TemperatureThe solution was cooled in the refrigerator overnight
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated

Procedure

To a 0° C. cold solution of 6.3 g of 3-[2-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-acrylic acid tert-butyl-dimethyl-silyl ester and 8 drops of DMF in 15 ml of CH2Cl2 was added dropwise 2.0 ml of oxalyl chloride. After complete addition the reaction mixture was allowed to warm to room temperature and stirring was continued for 60 h. The reaction mixture was filtered, evaporated to dryness and taken up in MTBE. The solution was cooled in the refrigerator overnight, filtered and evaporated to yield 4.4 g of 3-[2-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-acryloyl chloride.

Source