Dimethyl acetylenedicarboxylate → HCID 21187974, compound

HRID 1383434Notes

Reaction equation

HRID 1383434 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.[C:19]([C:25]([O:27][CH3:28])=[O:26])#[C:20][C:21]([O:23][CH3:24])=[O:22]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:24][O:23][C:21]([C:20]1[N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19]=1[C:25]([O:27][CH3:28])=[O:26])=[O:22]

Participants

5

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 21187972HCID 21187972, compound

Product 1

HCID 21187974HCID 21187974, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7,4 g of 2-(2-methoxyphenyl)amino-1-phenyl-ethan-1-one and 11,3 ml of dimethyl acetylenedicarboxylate in 150 ml of toluene is refluxed for 12 hours and then the solvent is eliminated in vacuo. The residue remaining is taken up in ethyl acetate and washed with water. After the organic phase has been dried the solvent is distilled off in vacuo and the residue remaining is chromatographed on silica gel (n-hexane:ethyl acetate 80:20). 9,4 g of 2,3-di(methoxycarbonyl)-1-(2-methoxyphenyl)-4-phenyl-pyrrole are obtained as a colourless oil.

Workup

  1. washwashed with water
  2. customAfter the organic phase has been dried the solvent
  3. distillationis distilled off in vacuo
  4. customthe residue remaining is chromatographed on silica gel (n-hexane:ethyl acetate 80:20)

Sources & evidence

ORD record
ord-14cb11fc6ed44a719c5a90c536707267
Source dataset
uspto-grants-2001_07
Patent number
US06255327B1

Reaction notes

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