Methanol → methyl 4-iodo-1H-pyrrole-2-carboxylate
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]=1Participants
6
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
- customthe reaction medium evaporated to dryness
- customthe residue obtained
- customThe organic phase was decanted off
- dry with materialdried over magnesium sulfate
- customevaporated
- customThe residue obtained
- customwas triturated in heptane
- filtrationfiltered
- 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
Reaction notes
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