Ethanol → HCID 54484409, compound

HRID 1389121Notes

Reaction equation

HRID 1389121 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:7](Cl)(=[O:11])[C:8](Cl)=[O:9].CC1NC=CC=1.[CH2:19]([OH:21])[CH3:20]>C(Cl)Cl>[CH2:19]([O:21][C:7](=[O:11])[C:8]([C:6]1[NH:1][C:3]([CH3:2])=[CH:4][CH:5]=1)=[O:9])[CH3:20]

Participants

6

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 124892-MethylpyrroleHCID 65578Oxalyl chloride

Product 1

HCID 54484409HCID 54484409, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Pyridine (8.80 g.) in dry methylene chloride (100 ml.) was added dropwise to a stirred solution of oxalyl chloride (13.96 g.) in dry methylene chloride (300 ml.) at -70° to give a white precipitate. The mixture was stirred at -70° for 15 minutes and then a solution of 2-methylpyrrole (8.10 g.) in dry methylene chloride (75 ml.) was added over 30 minutes. The mixture was stirred at -70° for a further 3 hours and then allowed to warm up to -20° giving a clear solution. Ethanol (25 ml.) was added and the solution was allowed to reach room temperature. The solution was washed with N hydrochloric acid (3×100 ml.) followed by water (3×100 ml.) and then dried over sodium sulphate. Evaporation of the solvent gave a dark oil which solidified on standing. The solid was dissolved in hot petroleum ether (B.P. 60°-80°) and some insoluble material was filtered off. The solid which crystallized from the cooled filtrate was chromatographed on silica gel. Elution with a mixture of chloroform and petroleum ether (B.P. 60°-80°) (3:1) gave a solid which was crystallized from petroleum ether (B.P. 60°-80°) to give 5-methyl-2-pyrrolylglyoxylic acid ethyl ester (11.4 g.), M.P. 72°-74°. Found: C, 59.72; H, 6.54; N, 7.47. C9H11NO3 requires: C, 59.66; H, 6.16; N, 7.77%.

Workup

  1. customto give a white precipitate
  2. stirringThe mixture was stirred at -70° for a further 3 hours
  3. temperatureto warm up to -20°
  4. customgiving a clear solution
  5. customto reach room temperature
  6. washThe solution was washed with N hydrochloric acid (3×100 ml.)
  7. dry with materialdried over sodium sulphate
  8. customEvaporation of the solvent
  9. customgave a dark oil which
  10. filtrationsome insoluble material was filtered off
  11. customThe solid which crystallized from the cooled filtrate
  12. customwas chromatographed on silica gel
  13. washElution
  14. additionwith a mixture of chloroform and petroleum ether (B.P. 60°-80°) (3:1)
  15. customgave a solid which
  16. customwas crystallized from petroleum ether (B.P. 60°-80°)

Sources & evidence

ORD record
ord-3e08834880434b8d8607786d24689e1d
Source dataset
uspto-grants-1981_01
Patent number
US04243672

Reaction notes

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