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

HRID 1479145Notes

Reaction equation

HRID 1479145 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-a3eabb3fe3064ed1b17867d244572c3d
Source dataset
uspto-grants-2016_08
Patent number
USRE046097E1

Reaction notes

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