Reaction #324413

Reaction equation

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

oxalyl dichloride

→

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

Solvents

CH2Cl2

Conditions

Workup

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

Procedure

Under an argon atmosphere, to a solution of 2-[4-(tert-butyldimethylsilyloxy)phenyl]acetic acid (9) (1.55 g, 5.82 mmol) in CH2Cl2 (10 mL) was added DMF (3 drops) by a Pasteur pipette at room temperature. To this was added oxalyl dichloride (1.00 mL, 11.8 mmol) at 0° C. and the mixture was stirred for an hour 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