Potassium Carbonate → methyl 3-(2-formyl-1H-pyrrol-1-yl)benzoate

HRID 399821Notes

Reaction equation

HRID 399821 reaction equation
P(Cl)(Cl)(Cl)=O.[N:6]1([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([O:16][CH3:17])=[O:15])[CH:10]=[CH:9][CH:8]=[CH:7]1.[C:21](=O)([O-])[O-:22].[K+].[K+]>CN(C)C=O>[CH:21]([C:10]1[N:6]([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([O:16][CH3:17])=[O:15])[CH:7]=[CH:8][CH:9]=1)=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 3322314Methyl 3-(1H-pyrrol-1-yl)benzoate

Product 1

HCID 17604923methyl 3-(2-formyl-1H-pyrrol-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Phosphoryl chloride (5.5 ml) was dropwise added to N,N-dimethylformamide (4.6 ml) under ice-cooling and the mixture was stirred for 15 minutes at 40°-50° C. To the mixture was added a solution of methyl 3-(pyrrol-1-yl)benzoate (6.0 g) in N,N-dimethylformamide (30 ml) at ambient temperature and the whole was stirred for 3 hours at 110°-120° C. An ice-cooling mixture was poured into ice-water and the mixture was adjusted to pH 9 with potassium carbonate. The mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give methyl 3-(2-formylpyrrol-1-yl)benzoate (5.31 g).

Workup

  1. temperaturecooling
  2. stirringthe whole was stirred for 3 hours at 110°-120° C
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-ef3fcd1027f24a20811cfc1409b2fff9
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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