Hydrochloric Acid → HCID 11687105, compound

HRID 749599Notes

Reaction equation

HRID 749599 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.[BH4-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([CH:8]([C:9]#[N:10])[C:11]#[N:12])[CH3:7])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2636762-[1-(4-chlorophenyl)ethylidene]malononitrileHCID 4311764Sodium borohydride

Product 1

HCID 11687105HCID 11687105, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

First, 3.00 g of (4-chloro-α-methylbenzylidene)malononitrile was dissolved in 20 ml of ethanol, and while stirring at room temperature, a suspension of 0.15 g of sodium borohydride in 5 ml of ethanol was added dropwise, followed by stirring at room temperature for 30 minutes. Then, 10% hydrochloride acid was added to the reaction mixture, which was extracted with diethyl 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 1.70 g of (1-(4-chlorophenyl)ethyl)malononitrile (the intermediate (6)).

Workup

  1. additionwas added dropwise
  2. stirringby stirring at room temperature for 30 minutes
  3. extractionwas extracted with diethyl 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-8c8ee4e1f9054cd1951d118cea2b07b7
Source dataset
uspto-grants-2008_07
Patent number
US07402691B2

Reaction notes

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