Methanol → Methyl pyrrole-2-carboxylate

HRID 1982382Notes

Reaction equation

HRID 1982382 reaction equation
[CH3:1][O-:2].[Na+].[Na].ClC(Cl)(Cl)C([C:9]1[NH:10][CH:11]=[CH:12][CH:13]=1)=O.[CH3:16][OH:17]>>[NH:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[C:1]([O:17][CH3:16])=[O:2]

Participants

5

Reactant 4

HCID 887Methanol2×HCID 3214872-(Trichloroacetyl)pyrroleHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 136930Methyl pyrrole-2-carboxylate

Procedure

A solution of sodium methoxide, prepared by dissolving sodium (34.0 g) in 4.0 L of methanol, is added to a solution of 2480 g of 2-(trichloroacetyl)-pyrrole in 6.0 L of methanol over a period of 1.5 hours under an atmosphere of nitrogen. There is an exotherm to 35° during the addition. Stirring is continued at room temperature for 2.5 hours, then the solution is concentrated to dryness in vacuo. The residue is dissolved in 9.0 L of ether and the solution is washed with 2×700 mL of water, dried over anhydrous magnesium sulfate (250 g), and stirred for 1 hour with charcoal (20 g). The mixture is filtered and the filtrate is concentrated to dryness to vacuo to give methyl pyrrole-2-carboxylate, m.p. 73°-74'.

Workup

  1. customto 35°
  2. additionduring the addition
  3. concentrationthe solution is concentrated to dryness in vacuo
  4. dissolutionThe residue is dissolved in 9.0 L of ether
  5. washthe solution is washed with 2×700 mL of water
  6. dry with materialdried over anhydrous magnesium sulfate (250 g)
  7. stirringstirred for 1 hour with charcoal (20 g)
  8. filtrationThe mixture is filtered
  9. concentrationthe filtrate is concentrated to dryness to vacuo

Sources & evidence

ORD record
ord-86a42aecbfa54a6b800d4fe9e55bf5a0
Source dataset
uspto-grants-1986_06
Patent number
US04596799

Reaction notes

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