Oxalyl chloride → 3-Trimethylsilylpropanoyl chloride

HRID 1440990Notes

Reaction equation

HRID 1440990 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[CH2:3][CH2:4][C:5](O)=[O:6].C(Cl)(=O)C([Cl:13])=O>CN(C)C=O.C(OCC)C>[CH3:1][Si:2]([CH3:9])([CH3:8])[CH2:3][CH2:4][C:5]([Cl:13])=[O:6]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 797643-(Trimethylsilyl)propionic acid

Product 1

HCID 5644893-Trimethylsilylpropanoyl chlorideYield 68.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

In a flask were place 13.4 g (0.0918 mole) of 4,4-dimethyl-4-silapentanoic acid, 100 mL of diethyl ether, and two drops of N,N-dimethylformamide. To this solution, which was cooled in an ice/water bath, was added 13.98 g (0.110 mole) of oxalyl chloride in diethyl ether in a dropwise manner. Upon completion of addition, the temperature was allowed to rise to ambient conditions, and the mixture was stirred for approximately 16 hours. At the conclusion of this period the solvent was evaporated from the reaction mixture under reduced pressure, leaving 10.42 g of 4,4-dimethyl-4-silapentanoic acid chloride as a residue. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customIn a flask were
  2. temperatureTo this solution, which was cooled in an ice/water bath
  3. additionUpon completion of addition
  4. customAt the conclusion of this period the solvent was evaporated from the reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-ee8e55c0c7b6484c8c39c6024a78cddd
Source dataset
uspto-grants-1996_03
Patent number
US05502054

Reaction notes

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