HCID 86745412, compound → HCID 15023291, compound

HRID 129332Notes

Reaction equation

HRID 129332 reaction equation
[CH2:1]1SSO[C:4]([C:8]2[CH:12]=[C:11]([C:13](=O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[NH:10][CH:9]=2)([O:5]CC)[O:3][CH2:2]1>C(O)C.[Ni]>[CH2:13]([C:11]1[NH:10][CH:9]=[C:8]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:12]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 1

HCID 86745412HCID 86745412, compound

Product 1

HCID 15023291HCID 15023291, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3.74 g (9.1 mmol) of ethyl 5-tridecanoylpyrrole-3-carboxylate dithioethylene ketal prepared in Sythetic Example 5 and 30 ml of Raney-nickel in 200 ml of ethanol was heated under reflux for 2 hours. After filteration through celite, the separated Raney-nickel was washed well with ethanol. The solvent was removed under reduced pressure, the residue was purified by subjecting it to silica gel column chromatography (eluent: ethyl acetate/hexane=1/7) to obtain 2.60 g (89% yield) of ethyl 5-tridecylpyrrole-3-carboxylate, m.p. 59.5°-60.5° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. washAfter filteration through celite, the separated Raney-nickel was washed well with ethanol
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified

Sources & evidence

ORD record
ord-d7f73ae3fc89488c96dca56e55a54d64
Source dataset
uspto-grants-1995_11
Patent number
USRE035096

Reaction notes

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