Hydrochloric Acid → HCID 69491077, compound

HRID 1375934Notes

Reaction equation

HRID 1375934 reaction equation
[H-].[Na+].[C:3]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:4].[CH2:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1I)[CH3:12].Cl.[CH2:21](OCC)[CH3:22]>CN(C)C=O.[Cu]I>[CH2:9]([O:8][C:6](=[O:7])[C:5]([CH2:21][CH3:22])([C:3]#[N:4])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:11][CH3:12])[CH3:10]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 7764Ethyl cyanoacetateHCID 24758Sodium hydrideHCID 140367Benzene, 1-ethyl-2-iodo-

Product 1

HCID 69491077HCID 69491077, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
95 °C

Procedure

Sodium hydride, as a 60% mineral oil dispersion (240 mg, 6 mmol) was introduced into a dry round bottomed flask and dry N,N-dimethylformamide (12 ml) was added thereto. The flask was stoppered with a serum cap and flushed with argon. A solution of ethyl cyanoacetate (679 mg, 6 mmol) in N,N-dimethylformamide (3 ml) was added dropwise to the stirred slurry and the reaction was stirred for 10 minutes after the addition was complete. 2-Ethyl iodobenzene was then added in one portion, followed by copper (I) iodide (1143 mg, 6 mmol). The mixture was heated at 95° C. for 4 h, then cooled to 0° C. and poured into 1 N hydrochloric acid (100 ml). Diethyl ether was added; the aqueous layer was removed and extracted again with 3×100 ml of diethyl ether. The ethereal extracts were combined, dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The oily residue was purified by flash chromatography using hexane:ethyl acetate: dichlorometane 8:1:1 as eluent, obtaining 326 mg of ethyl cyano(2-ethylphenyl) acetic acid ethyl ester as a colourless oil. Yield 50%.

Workup

  1. customcap
  2. customflushed with argon
  3. additionafter the addition
  4. temperaturecooled to 0° C.
  5. customthe aqueous layer was removed
  6. extractionextracted again with 3×100 ml of diethyl ether
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was removed under reduced pressure
  10. customThe oily residue was purified by flash chromatography

Sources & evidence

ORD record
ord-4985cdfd0f024a88b779260c47c07356
Source dataset
uspto-grants-2007_01
Patent number
US07169890B2

Reaction notes

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