Acetonitrile → HCID 15688742, compound

HRID 2416954Notes

Reaction equation

HRID 2416954 reaction equation
I[Si](C)(C)C.C(#N)C.[Cl:9][CH2:10][CH2:11][CH2:12][C:13]([CH3:20])([CH3:19])[C:14]([O:16]CC)=[O:15]>O>[Cl:9][CH2:10][CH2:11][CH2:12][C:13]([CH3:20])([CH3:19])[C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 85247Trimethylsilyl iodideHCID 114240955-Chloro-2,2-dimethylpentanoic acid ethyl ester

Product 1

HCID 15688742HCID 15688742, compoundYield 109.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Iodotrimethylsilane (3.00 g, 15 mmols) was added to an acetonitrile solution (5 ml) of ethyl 5-chloro-2,2-dimethylpentanoate (963 mg, 5 mmols) at room temperature, and heated at 80° C. for 24 hours with stirring. The reaction mixture was poured into water with ice, and extracted with ether. The organic layer was washed with water, and dried with anhydrous magnesium sulfate, and the solvent was evaporated to obtain 0.9 g of 5-chloro-2,2-dimethylpentanoic acid as a brown oil.

Workup

  1. extractionextracted with ether
  2. washThe organic layer was washed with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-68ed247a54704339a08fedca0ee3a31a
Source dataset
uspto-grants-2004_11
Patent number
US06825223B2

Reaction notes

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