Diethyl Oxalate → 3-hydroxy-1,4-diphenyl-1H-pyrrole-2,5-dione

HRID 929482Notes

Reaction equation

HRID 929482 reaction equation
[C:1]1([NH:7][C:8](=[O:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:19][C:20](=O)[C:21](OCC)=[O:22])C.CC(C)([O-])C.[K+]>O>[OH:22][C:21]1[C:20](=[O:19])[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8](=[O:16])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 225533N,2-DiphenylacetamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 546840203-hydroxy-1,4-diphenyl-1H-pyrrole-2,5-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After the addition of anhydride THF (20 ml) to compound 5a (1.55 g, 7.34 mmol), the temperature was adjusted to 0° C. Diethyloxalate (1.45 g, 9.50 mmol) and potassium t-butoxide (1.35 g, 11.9 mmol) were added thereto and the agitation for 3 hours was carried out. After the identification of the reaction progress with TLC, the solution was poured into the distilled water and acidified with 1N HCL aqueous solution. Three times extractions were carried out with EA and three times washings were carried out with brine. Water was removed by using Na2SO4, solvents were removed and then, the suspension was carried out by HX.

Workup

  1. customwas adjusted to 0° C
  2. extractionThree times extractions
  3. customWater was removed
  4. customwere removed

Sources & evidence

ORD record
ord-d316cb481a6947ba801bc7773ce18bc5
Source dataset
uspto-grants-2016_03
Patent number
US09296690B2

Reaction notes

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