Chlorotrimethylsilane → Methyl pyrrole-2-carboxylate

HRID 1698911Notes

Reaction equation

HRID 1698911 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=[O:7].[CH3:9][Si](Cl)(C)C>CO>[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 12473Pyrrole-2-Carboxylic Acid

Product 1

HCID 136930Methyl pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of pyrrole-2-carboxylic acid (6.28 g, 56.5 mmol) in anh. MeOH (100 mL) under N2 at room temp. was added TMSCl (17.9 mL, 141 mmol, 2.5 equiv) in one portion. After stirring overnight, the reaction mixture was concentrated under reduced pressure, redissolved in CH2Cl2, washed with water, dried (Na2SO4) and concentrated to give methyl pyrrole-2-carboxylate as a tannish semi-crystalline solid (4.62 g, 65%): 1H NMR (CDCl3) δ3.86 (s, 3H), 6.29 (br q, 1H), 6.92 (br m, 1H), 6.96 (br m, 1H), 9.30 (br s, 1H). This material was used in the next step without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionredissolved in CH2Cl2
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-024bb681e2474e2dbd4c374a4c8be1bd
Source dataset
uspto-grants-2002_02
Patent number
US06344476B1

Reaction notes

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