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

HRID 237211Notes

Reaction equation

HRID 237211 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) (1.55 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.

Workup

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

Sources & evidence

ORD record
ord-88b2422d3c444cf5872ec48f5d5010c4
Source dataset
uspto-grants-2014_02
Patent number
US08642281B2

Reaction notes

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