Oxalyl chloride → 2-[4-(Tert-butyldimethylsilyloxy)phenyl]acetyl chloride

HRID 333622Notes

Reaction equation

HRID 333622 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(Cl)(=O)C([Cl:22])=O>C(Cl)Cl.CN(C=O)C>[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([Cl:22])=[O:18])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 6106182-{4-[(Tert-butyldimethylsilyl)oxy]phenyl}acetic acid

Product 1

HCID 121887072-[4-(Tert-butyldimethylsilyloxy)phenyl]acetyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

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.

Workup

  1. temperaturethe mixture was heated
  2. customwhile elevating to room temperature
  3. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-669c38815b6e459095fc743e5bb707a5
Source dataset
uspto-grants-2014_11
Patent number
US08883432B2

Reaction notes

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