Ethyl Acetate → HCID 58083493, compound

HRID 1254002Notes

Reaction equation

HRID 1254002 reaction equation
[CH2:1]([N:3]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6](I)[C:5]([CH3:13])=[N:4]1)[CH3:2].[Cu][C:15]#[N:16].CCOC(C)=O>CN(C=O)C>[C:15]([C:6]1[C:5]([CH3:13])=[N:4][N:3]([CH2:1][CH3:2])[C:7]=1[C:8]([O:10][CH3:11])=[O:9])#[N:16]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 58083500HCID 58083500, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 58083493HCID 58083493, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask, methyl 1-ethyl-4-iodo-3-methylpyrazol-5-ylcarboxylate (1.00 g, 0.003 mol) was dissolved in 10 mL of DMF and copper (I) cyanide (0.46 g, 0.005 mol) was added in batches. After heating to reflux for 1 h, the mixture was separated by filtration. The filtrate was diluted with 50 mL of water, and then extracted with 50 mL of ethyl acetate. The organic layer was washed with 50 mL of saturated aqueous sodium bicarbonate solution and 50 mL of saturated brine, dried over anhydrous MgSO4 and concentrated under reduced pressure. Column chromatography (EtOAc:P.E.=1:10 as eluent) gave 0.53 g of the title compound as a yellow oil (yield 80%).

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 1 h
  3. customthe mixture was separated by filtration
  4. additionThe filtrate was diluted with 50 mL of water
  5. extractionextracted with 50 mL of ethyl acetate
  6. washThe organic layer was washed with 50 mL of saturated aqueous sodium bicarbonate solution and 50 mL of saturated brine
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e6a6db3d842a45a39921fc8f640ba3af
Source dataset
uspto-grants-2013_06
Patent number
US08455532B2

Reaction notes

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