Acetic Acid → 2-(1-(Trimethylsilyl)ethylidene) malononitrile

HRID 2410261Notes

Reaction equation

HRID 2410261 reaction equation
[C:1]([Si:4]([CH3:7])([CH3:6])[CH3:5])(=O)[CH3:2].[C:8](#[N:12])[CH2:9][C:10]#[N:11].C([O-])(=O)C.[NH4+].C(O)(=O)C>CCOC(C)=O.C1C=CC=CC=1>[CH3:5][Si:4]([CH3:7])([CH3:6])[C:1](=[C:9]([C:8]#[N:12])[C:10]#[N:11])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8010MalononitrileHCID 517165Ammonium AcetateHCID 638116Acetyltrimethylsilane

Product 1

HCID 866915002-(1-(Trimethylsilyl)ethylidene) malononitrileYield 80%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

To a mixture of acetyltrimethylsilane (1.0 g, 8.6 mmol), malononitrile (625 mg, 9.46 mmol) and ammonium acetate (126 mg, 1.64 mmol), acetic acid (394 μL, 6.88 mmol) and benzene (30 mL) were added. The reaction flask was attached to a Dean-Stark trap filled with benzene and the solution was heated to 95° C. for 3 h. The orange reaction mixture was cooled, diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, and concentrated. The residue was purified by column chromatography on silica gel (using a solvent gradient from 1% to 30% EtOAc in hexanes) to give 2-(1-(trimethylsilyl)ethylidene) malononitrile as colorless oil (1.13 g, 79.8%).

Workup

  1. additionwere added
  2. temperatureThe orange reaction mixture was cooled
  3. washwashed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (

Sources & evidence

ORD record
ord-2b503b0e1b0a411fbd1a24a275d5ecc6
Source dataset
uspto-grants-2014_08
Patent number
US08816082B2

Reaction notes

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