Hydrochloric Acid → (4-(Trifluoromethoxy)benzyl)malononitrile

HRID 1743622Notes

Reaction equation

HRID 1743622 reaction equation
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:15]=[CH:14][C:7]([CH:8]=[C:9]([C:12]#[N:13])[C:10]#[N:11])=[CH:6][CH:5]=1.[BH4-].[Na+].Cl>O1CCCC1.C(O)C>[F:1][C:2]([F:16])([F:17])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH:9]([C:12]#[N:13])[C:10]#[N:11])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8456624-(Trifluoromethoxy)benzalmalononitrileHCID 4311764Sodium borohydride

Product 1

HCID 22235052(4-(Trifluoromethoxy)benzyl)malononitrileYield 83.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Then, 2.61 g of (4-(trifluoromethoxy)benzylidene)malononitrile was dissolved in 20 ml of tetrahydrofuran, and while stirring at room temperature, a suspension of 0.11 g of sodium borohydride in 5 ml of ethanol was added dropwise, followed by stirring at room temperature for 30 minutes. Then, 10% hydrochloric acid was added, and the mixture 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 2.20 g of (4-(trifluoromethoxy)benzyl)malononitrile (the intermediate (7)).

Workup

  1. additionwas added dropwise
  2. stirringby stirring at room temperature for 30 minutes
  3. extractionthe mixture was 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-e5f1e74809874391ba0b9041f0b701ba
Source dataset
uspto-grants-2006_03
Patent number
US07011838B2

Reaction notes

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