Ethylene Glycol → 3-Tridecylpyrrole

HRID 465399Notes

Reaction equation

HRID 465399 reaction equation
[CH2:1]([C:14]1[CH:15]=[C:16](C(OC)=O)[NH:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C(O)CO.[OH-].[K+]>O>[CH2:1]([C:14]1[CH:15]=[CH:16][NH:17][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 15023274Methyl 4-tridecylpyrrole-2-carboxylate

Product 1

HCID 198748193-TridecylpyrroleYield 97.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
190 °C

Procedure

Into a mixture of 9.50 g (30.9 mmol) of methyl 4-tridecylpyrrole-2-carboxylate obtained in Synthesis Example 3,200 ml of ethylene glycol and 10 ml of water, was added 20 g of potassium hydroxide and the mixture was heated at 190° C. under stirring for 5 hours. After cooling, the mixture was added with water and extracted with ethyl acetate. The organic layer was collected, washed with water, dried over anhydrous magnesium sulfate and then evaporated. The residue was purified by a silica-gel column chromatography (eluent: ethyl acetate/hexane=1/5) to obtain 7.50 g of 3-tridecylpyrrole. The yield was 97% and the melting point was 32.5° to 33.5° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was collected
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by a silica-gel column chromatography (eluent: ethyl acetate/hexane=1/5)

Sources & evidence

ORD record
ord-b0f8eef652b34e2ca3bcbb818e6610ee
Source dataset
uspto-grants-1992_10
Patent number
US05153217

Reaction notes

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