Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 70435233, compound

HRID 255675Notes

Reaction equation

HRID 255675 reaction equation
[CH:1]([C:3]1[N:4]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=2[CH3:20])[CH:5]=[C:6]([C:10](=[O:12])[CH:11]=1)[C:7]([OH:9])=[O:8])=O.[CH2:21]([O:23][C:24]([CH:26]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:25])[CH3:22]>CO>[CH2:21]([O:23][C:24]([CH:26]=[CH:1][C:3]1[N:4]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=2[CH3:20])[CH:5]=[C:6]([C:10](=[O:12])[CH:11]=1)[C:7]([OH:9])=[O:8])=[O:25])[CH3:22]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 14010769HCID 14010769, compound

Product 1

HCID 70435233HCID 70435233, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 5 ml of methanol was dissolved 0.15 g of 6-formyl-1-(4-hydroxy-2-methylphenyl)-4-oxo-1,4-dihydronicotinic acid, and 0.19 g of ethoxycarbonylmethylenetriphenylphosphorane was added thereto. They were reacted at room temperature for one hour. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform/ethanol (50:1 by volume) mixture) to obtain 0.06 g of 6-(2-ethoxycarbonylethenyl)-1-(4-hydroxy-2-methylphenyl)-4-oxo-1,4-dihydronicotinic acid having a melting point of 185°-189° C.

Workup

  1. additionwas added
  2. customThey were reacted at room temperature for one hour
  3. customAfter completion of the reaction
  4. customthe solvent was removed by distillation under reduced pressure
  5. customthe residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform/ethanol (50:1 by volume) mixture)

Sources & evidence

ORD record
ord-da2cec772ee342b1b3e9048c7adbdfcb
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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