Potassium Iodide → HCID 86709901, compound

HRID 341340Notes

Reaction equation

HRID 341340 reaction equation
Cl[CH2:2][Si:3]1([CH3:8])[CH2:7][CH2:6][CH2:5][CH2:4]1.[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10].[I-].[K+].[C:19](=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>C(#N)C>[CH3:8][Si:3]1([CH2:2][CH2:19][CH:11]([C:9]#[N:10])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 7764Ethyl cyanoacetateHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 14984321HCID 14984321, compound

Product 1

HCID 86709901HCID 86709901, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-chloromethyl-1-methyl-1-silacyclopentane (1.500 g, 10.1 mmol) and ethyl cyanoacetate (1.29 ml, 12.1 mmol) in acetonitrile (25 ml) was added with potassium iodide (2.01 g, 12.1 mmol) and potassium carbonate (2.09 g, 15.1 mmol), and the mixture was stirred for 38 hours under reflux by heating. The reaction vessel was cooled on ice, the reaction mixture was added with saturated aqueous ammonium chloride, and the mixture was extracted with ethyl acetate. The organic layer was treated in a conventional manner, and the residue was purified by silica gel column chromatography [hexane/ethyl acetate (9:1)] to obtain ethyl 3-[(1-methyl-1-silacyclopentan-1-yl)methyl]-2-cyanopropionate (1.449 g, 64%) as colorless oil.

Workup

  1. temperatureunder reflux
  2. temperatureby heating
  3. temperatureThe reaction vessel was cooled on ice
  4. extractionthe mixture was extracted with ethyl acetate
  5. additionThe organic layer was treated in a conventional manner
  6. customthe residue was purified by silica gel column chromatography [hexane/ethyl acetate (9:1)]

Sources & evidence

ORD record
ord-caaf95def6fe43abbe6ebdba026bf0f4
Source dataset
uspto-grants-2014_11
Patent number
US08895769B2

Reaction notes

Loading…