Chlorotrimethylsilane → Methyl pyrrole-2-carboxylate

HRID 635241Notes

Reaction equation

HRID 635241 reaction equation
Cl[Si](C)(C)[CH3:3].[NH:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]([OH:13])=[O:12]>CO>[NH:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]([O:13][CH3:3])=[O:12]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 12473Pyrrole-2-Carboxylic Acid

Product 1

HCID 136930Methyl pyrrole-2-carboxylateYield 65.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Chlorotrimethylsilane (17.9 mL, 141 mmol, 2.5 equiv) is added in one portion to a solution of pyrrole-2-carboxylic acid (6.28 g, 56.5 mmol) in dry methanol (100 mL) under N2 at rt. After stirring overnight, the reaction mixture is concentrated in vacuo, redissolved in dichloromethane, washed with water, dried (Na2SO4) and concentrated to give 4.62 g of methyl pyrrole-2-carboxylate as a tannish semi-crystalline solid (65%), which was used without further purification. 1H NMR (CDCl3) d 9.3 (br s, 1H), 6.96 (br m, 1H), 6.92 (br m, 1H), 6.29 (br q, 1H), 3.86 (s, 3H).

Workup

  1. concentrationthe reaction mixture is concentrated in vacuo
  2. dissolutionredissolved in dichloromethane
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d9311924afcc4c5b88cfb7857fbde833
Source dataset
uspto-grants-2001_02
Patent number
US06187799B1

Reaction notes

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