Reaction #324411

Reaction equation

2-[4-(tert-butyldimethylsilyloxy)phenyl]acetic acid

oxalyl dichloride

→

2-[4-(tert-butyldimethylsilyloxy)phenyl]acetyl chloride

Solvents

CH2Cl2

Conditions

Workup

1. 1
   Temperaturethe mixture was heated
2. 2
   Otherwhile elevating to room temperature
3. 3
   ConcentrationThe mixture was concentrated under reduced pressure

Procedure

Under an argon atmosphere, to a solution of 2-[4-(tert-butyldimethylsilyloxy)phenyl]acetic acid (9) (1.40 g, 5.26 mmol) in CH2Cl2 (10 mL) was added DMF (3 drops) by a Pasteur pipette at room temperature. To this was added oxalyl dichloride (890 μL, 10.5 mmol) at 0° C. and the mixture was heated with stirring for 30 minutes while elevating to room temperature. The mixture was concentrated under reduced pressure to give crude 2-[4-(tert-butyldimethylsilyloxy)phenyl]acetyl chloride (10) as a colorless oil, which was used in the following reaction without further purification.

Source