Methyl formate → Methyl 2-{2-hydroxy-1-[(methyloxy)carbonyl]ethenyl}-1-methyl-1H-pyrrole-3-carboxylate

HRID 733715Notes

Reaction equation

HRID 733715 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[CH:8][N:7]([CH3:10])[C:6]=1[CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:4].[H-].[Na+].[CH:18](OC)=[O:19]>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[CH:8][N:7]([CH3:10])[C:6]=1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:18][OH:19])=[O:4]

Participants

5

Reactant 3

HCID 7865Methyl formateHCID 24758Sodium hydrideHCID 44475349methyl 2-(2-methoxy-2-oxoethyl)-1-methyl-1H-pyrrole-3-carboxylate

Product 1

HCID 68867490Methyl 2-{2-hydroxy-1-[(methyloxy)carbonyl]ethenyl}-1-methyl-1H-pyrrole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methoxycarbonylmethyl-1-methyl-1H-pyrrole-3-carboxylic acid methyl ester (5.7 g) in dry tetrahydrofuran (100 ml) was stirred at room temperature under argon. Sodium hydride (60% dispersion in mineral oil, 7.13 g) was added portionwise followed by methyl formate (2.5 ml) and the mixture was left to stir overnight. The reaction was cooled in ice and quenched by the addition of the minimum amount of methanol. The solution was again cooled and acidified to pH1 with aqueous 5N hydrochloric acid. The reaction was diluted with ethyl acetate and water, the aqueous separated and extracted three times with ethyl acetate. The combined organic layers were then washed with brine, dried (MgSO4) and filtered. The solvent was evaporated to yield an oil consisting of two layers. The top layer was discarded and the lower layer solidified on standing to give the crude title compound as a brown solid (8.62 g).

Workup

  1. waitthe mixture was left
  2. temperatureThe reaction was cooled in ice
  3. customquenched by the addition of the minimum amount of methanol
  4. temperatureThe solution was again cooled
  5. additionThe reaction was diluted with ethyl acetate and water
  6. customthe aqueous separated
  7. extractionextracted three times with ethyl acetate
  8. washThe combined organic layers were then washed with brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customThe solvent was evaporated
  12. customto yield an oil

Sources & evidence

ORD record
ord-7358b4299d4a4b3ea7de25e6c49c8e1a
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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