Dimethylformamide → (E)-Methyl 3-(4-methoxyphenyl)acrylate

HRID 368908Notes

Reaction equation

HRID 368908 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:10]([O:14][CH3:15])(=[O:13])[CH:11]=[CH2:12].C(N(CCCC)CCCC)CCC.CN(C=O)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:15][O:14][C:10](=[O:13])/[CH:11]=[CH:12]/[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7294Methyl AcrylateHCID 7622TributylamineHCID 696764-Iodoanisole

Product 1

HCID 641297(E)-Methyl 3-(4-methoxyphenyl)acrylateYield 70%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

Table 1, Entry 1. In the reaction tube were mixed 4-iodoanisole (0.234 g, 1.0 mmol), methyl acrylate (0.108 g, 1.25 mmol), palladium acetate (0.00225 g, 0.01 mmol), tri-n-butylamine (0.185 g, 1.0 mmol) and 0.50 ml DMF.under nitrogen. The contents of the flask were irradiated for 3.50 min with an effect of 60 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 (4/1) as the eluent. The yield was 70% (white solid).

Workup

  1. customThe contents of the flask were irradiated for 3.50 min with an effect of 60 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-037bb0e53ce44d51a10c2dc72eedef2c
Source dataset
uspto-grants-2000_10
Patent number
US06136157

Reaction notes

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