Methyl iodide → HCID 13601672, compound

HRID 1004232Notes

Reaction equation

HRID 1004232 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[O:15])/[CH:10]=[CH:11]/[C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[Cl:8].I[CH3:17]>CN(C=O)C.C1CCN2C(=NCCC2)CC1>[CH3:17][O:13][C:12](=[O:14])/[CH:11]=[CH:10]/[C:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)=[O:15]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 6172511(E)-4-(3,4-dichlorophenyl)-4-oxo-but-2-enoic acid

Product 1

HCID 13601672HCID 13601672, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneSolvent

Procedure

To an ice cooled solution of (E)-4-(3',4'-dichlorophenyl)-4-oxo-2-butenoic acid (2.4 g, 0.01 mol) in dry DMF (80 mL), DBU (1.5 mL, 0.01) was added dropwise on stirring, under nitrogen atmosphere. To the resulting stirred solution iodomethane (3.1 mL, 0.05 mol) dissolved in dry DMF (20 mL) was added dropwise over 20 min. The resulting solution was stirred at 0° C. for 1 hour and 3 hours at room temperature. The resulting reaction mixture was poured into ice-water on stirring, and the precipitate was filtered, washed with water and then with hexane. Recrystallization from diisopropyl ether/hexane provided the pure ester (2.2 g, 86%), pale yellow needles, mp. 108-109°.

Workup

  1. additionwas added dropwise over 20 min
  2. stirringThe resulting solution was stirred at 0° C. for 1 hour and 3 hours at room temperature
  3. customThe resulting reaction mixture
  4. stirringon stirring
  5. filtrationthe precipitate was filtered
  6. washwashed with water
  7. customRecrystallization from diisopropyl ether/hexane

Sources & evidence

ORD record
ord-8a990e93bfea45e3a99a2b7df774c564
Source dataset
uspto-grants-2000_04
Patent number
US06048896

Reaction notes

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