Ethyl Acetate → Methyl 3-methylsulfonyl-5-(pyrrol-1-yl)benzoate

HRID 399791Notes

Reaction equation

HRID 399791 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].CO[CH:18]1[CH2:22][CH2:21][CH:20](OC)O1.C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.O>[CH3:15][S:12]([C:4]1[CH:5]=[C:6]([CH:11]=[C:2]([N:1]2[CH:18]=[CH:22][CH:21]=[CH:20]2)[CH:3]=1)[C:7]([O:9][CH3:10])=[O:8])(=[O:14])=[O:13]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 790982,5-DimethoxytetrahydrofuranHCID 18945412Methyl 3-amino-5-(methylsulfonyl)benzoate

Product 1

HCID 18945432Methyl 3-methylsulfonyl-5-(pyrrol-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

The mixture of methyl 5-amino-3-methylsulfonylbenzoate (1.5 g) and 2,5-dimethoxytetrahydrofuran (1.3 ml) in acetic acid (4.5 ml) was heated under reflux for 2 hours under stirring. After cooling, the mixture was poured into a mixture of ethyl acetate and water, and adjusted to pH 8 with 20% aqueous potassium carbonate solution. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was removed by concentration and the residue was triturated with diisopropyl ether to give methyl 3-methylsulfonyl-5-(pyrrol-1-yl)benzoate (1.58 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed by concentration
  7. customthe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-43600cd00ec94bc1aedc71ed6ce3b30a
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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