Sodium Methoxide → methyl 4-iodo-1H-pyrrole-2-carboxylate

HRID 899373Notes

Reaction equation

HRID 899373 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[NH:6][CH:7]=[C:8]([I:10])[CH:9]=1)=[O:4].[CH3:13][O-:14].[Na+]>CO>[CH3:13][O:14][C:3]([C:5]1[NH:6][CH:7]=[C:8]([I:10])[CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 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-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of 2,2,2-trichloro-1-(4-iodo-1H-pyrrol-2-yl)ethanone (68 g, 201 mmol, 1.0 equivalent) in dry methanol (400 mL) under nitrogen, was added a solution of sodium methoxide in methanol (4.37 M, 54 mL, 235 mmol, 1.2 equivalents) over 10 minutes. The resulting mixture was stirred at room temperature for 1 hour. The volatiles were removed under reduced pressure and the crude was then partitioned between water and tert-butylmethyl ether. The organic phase was separated, washed two times with water, saturated sodium chloride, dried over sodium sulfate, filtered and concentrated under vacuum to afford the title compound (48 g, 96%) as a colorless solid, that was used directly without further purification.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe crude was then partitioned between water and tert-butylmethyl ether
  3. customThe organic phase was separated
  4. washwashed two times with water, saturated sodium chloride
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7ddc6df217804e61b831522e3d33f30b
Source dataset
uspto-grants-2008_04
Patent number
US07354939B2

Reaction notes

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