Hydrochloric Acid → HCID 22235030, compound

HRID 1743617Notes

Reaction equation

HRID 1743617 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([C:6](=[C:8]([C:11]#[N:12])[C:9]#[N:10])[CH3:7])=[CH:4][CH:3]=1.[CH3:15][Mg]I.Cl>C(OCC)C.[Cu]I>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH:8]([C:11]#[N:12])[C:9]#[N:10])([CH3:15])[CH3:7])=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2636762-[1-(4-chlorophenyl)ethylidene]malononitrileHCID 178418373HCID 178418373, compound

Product 1

HCID 22235030HCID 22235030, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Solvent

Procedure

First, 1.00 g of (4-chloro-α-methylbenzylidene)malononitrile of the formula: was dissolved in 20 ml of diethyl ether, to which a catalytic amount of copper (I) iodide was added, and while stirring under ice cooling, a solution of methyl magnesium iodide in diethyl ether (prepared from 0.30 g of magnesium, 10 ml of diethyl ether, and 0.86 ml of methyl iodide) was added dropwise, followed by stirring for 30 minutes under ice cooling. Then, 10% hydrochloric acid was added to the reaction mixture, which was extracted with ethyl ether. The organic layer was successively washed with 10% hydrochloric acid, a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.74 g of (1-(4-chlorophenyl)-1-methylethyl)malononitrile (the intermediate (2)).

Workup

  1. additionwas added
  2. stirringby stirring for 30 minutes under ice cooling
  3. extractionwas extracted with ethyl ether
  4. washThe organic layer was successively washed with 10% hydrochloric acid
  5. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c3be499209254e1ba9384ff5dac8c6c4
Source dataset
uspto-grants-2006_03
Patent number
US07011838B2

Reaction notes

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