Methanol → methyl 4-iodo-1H-pyrrole-2-carboxylate

HRID 1128

Reaction equation

HRID 1128 reaction equation
[I:1][C:2]1[CH:3]=[C:4](C(=O)C(Cl)(Cl)Cl)[NH:5][CH:6]=1.[CH3:13][OH:14].[CH3:15][O-:16].[Na+]>O.C(OCC)C>[I:1][C:2]1[CH:3]=[C:4]([C:13]([O:16][CH3:15])=[O:14])[NH:5][CH:6]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 116816022,2,2-trichloro-1-(4-iodo-1H-pyrrol-2-yl)ethan-1-one

Product 1

HCID 11673249methyl 4-iodo-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

8.2 g (24 mmol) of 4-iodo-2-trichloroacetylpyrrole and 100 ml of methanol were introduced into a round-bottomed flask and 2 g (36 mmol) of sodium methoxide were added. The mixture was stirred at room temperature for four hours, the reaction medium evaporated to dryness, and the residue obtained taken up in water and ethyl ether. The organic phase was decanted off, dried over magnesium sulfate and evaporated. The residue obtained was triturated in heptane and filtered; 4.9 g (81%) of the expected ester of melting point 77°-78° C. were recovered.

Workup

  1. customthe reaction medium evaporated to dryness
  2. customthe residue obtained
  3. customThe organic phase was decanted off
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. customwas triturated in heptane
  8. filtrationfiltered
  9. custom4.9 g (81%) of the expected ester of melting point 77°-78° C. were recovered

Sources & evidence

ORD record
ord-2f9353d568ba495d9d6fa8a66d2c0875
Source dataset
uspto-grants-1998_03
Patent number
US05723499

Linked notes

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