Dimethylformamide → 1-Naphthylacrylonitrile

HRID 368911

Reaction equation

HRID 368911 reaction equation
I[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[C:12](#[N:15])[CH:13]=[CH2:14].C(N(CC)CC)C.CN(C=O)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[C:2]1([C:13](=[CH2:14])[C:12]#[N:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 70041-IodonaphthaleneHCID 7855AcrylonitrileHCID 8471Triethylamine

Product 1

HCID 103522651-NaphthylacrylonitrileYield 90%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

Table 1, Entry 4. In the reaction tube were mixed 1-iodonaphthalene (0.254 g, 1.0 mmol), acrylonitrile (0.066 g, 1.25 mmol), palladium acetate (0.00225 g, 0.01 mmol), triethylamine (0.50 ml) and 0.50 ml DMF.under nitrogen. The contents of the flask were irradiated for 3.50 min with an effect of 80 W. After cooling, the product mixture was poured into 25 ml water and was extracted three times with 25 ml DCM. The combined extracts were washed with 25 ml water and concentrated to an oil. The crude product was purified by column chromatography on silica gel using i-hexane/diethyl ether (2/1) as the eluent. The yield was 90% (white solid, trans/cis 4/1).

Workup

  1. customThe contents of the flask were irradiated for 3.50 min with an effect of 80 W
  2. temperatureAfter cooling
  3. extractionwas extracted three times with 25 ml DCM
  4. washThe combined extracts were washed with 25 ml water
  5. concentrationconcentrated to an oil
  6. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6c5023654de6452b8cb31da81b2c133f
Source dataset
uspto-grants-2000_10
Patent number
US06136157

Linked notes

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