Triethylamine → 3-Indolizinecarboxylic acid, 2-(methylthio)-, ethyl ester

HRID 502477Notes

Reaction equation

HRID 502477 reaction equation
[Br-].[CH2:2]([O:4][C:5]([CH2:7][N+:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6])[CH3:3].[CH3:14][S:15][C:16](SC)=[CH:17][N+]([O-])=O.C(N(CC)CC)C>C(O)C>[CH3:14][S:15][C:16]1[CH:17]=[C:13]2[N:8]([C:7]=1[C:5]([O:4][CH2:2][CH3:3])=[O:6])[CH:9]=[CH:10][CH:11]=[CH:12]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 87028Pyridinium, 1-(2-ethoxy-2-oxoethyl)-, bromide (1:1)

Product 1

HCID 143998103-Indolizinecarboxylic acid, 2-(methylthio)-, ethyl esterYield 91.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-ethoxycarbonylmethylpyridinium bromide 5 (6.15 g, 25 mmol), 1,1-bis(methylsulphanyl)-2-nitroethylene (8.2 g, 50 mmol) and 25 g of triethylamine in 150 ml of ethanol was heated at reflux for 12 h. Following evaporation of the solvents and of the excess triethylamine, 150 ml of water were added to the residue, and the organic phase was extracted with petroleum ether (75 ml×3). The combined extracts were dried over anhydrous magnesium sulphate, filtered and then concentrated under vacuum. The residual oil was chromatographed on a neutral alumina column, with hexane as the eluting solvent, to give ethyl 2-(methylsulphanyl)-3-indolizinecarboxylate 9 (5.4 g).

Workup

  1. temperatureat reflux for 12 h
  2. customevaporation of the solvents
  3. additionof the excess triethylamine, 150 ml of water were added to the residue
  4. extractionthe organic phase was extracted with petroleum ether (75 ml×3)
  5. dry with materialThe combined extracts were dried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residual oil was chromatographed on a neutral alumina column, with hexane as the eluting solvent

Sources & evidence

ORD record
ord-8ae6693a82df445387d6865d1517edf7
Source dataset
uspto-grants-2010_08
Patent number
US07776107B2

Reaction notes

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