Acetonitrile → HCID 15688742, compound

HRID 1532711Notes

Reaction equation

HRID 1532711 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-f52bd1a6201040f9acaa7d64a7abcfef
Source dataset
uspto-grants-2001_03
Patent number
US06204278B1

Reaction notes

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