Triethylamine → HCID 20464711, compound

HRID 325415Notes

Reaction equation

HRID 325415 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6]1[N:7]([CH3:17])[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([CH3:11])[CH:10]=1)[CH3:2].C(N(CC)CC)C.[Se](=O)=[O:27]>N1C=CC=CC=1>[CH3:17][N:7]1[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([CH3:11])[CH:10]=[C:6]1[C:5](=[O:27])[C:4]([O:3][CH2:1][CH3:2])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24007Selenium DioxideHCID 20464782HCID 20464782, compound

Product 1

HCID 20464711HCID 20464711, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl-1,4 dimethyl-5-ethoxycarbonylpyrrole-2-acetate (26.3 g, 0.104 mol) is mixed with triethylamine (7.2 ml, 0.052 mol), pyridine (165 ml, dried over 4 A sieves) and selenium dioxide (12.9 g, 0.115 mol) under nitrogen. The mixture is stirred mechanically and is heated to 95°-100° for 6.5 hours. The reaction is then allowed to cool and the heterogeneous mixture is filtered through a bed of Celite and washed with ether until no further color comes through. The organic solution is then washed with 2 N HCl (4×200 ml), and the combined acid washes are backwashed with ether (150 ml). The combined ether layers are washed with saturated aqueous sodium bicarbonate (100 ml) and saturated brine (150 ml). The ether solution is dried over sodium sulfate and the solvent is removed to give a brown oil which crystallizes on standing. The product is purified by preparative HPLC (4/1 hexanes/ether) to give 14.5 g of ethyl 1,4-dimethyl-5-ethoxycarbonyl-α -oxopyrrole-2-acetate.

Workup

  1. temperatureis heated to 95°-100° for 6.5 hours
  2. temperatureto cool
  3. filtrationthe heterogeneous mixture is filtered through a bed of Celite
  4. washwashed with ether until no further color
  5. washThe organic solution is then washed with 2 N HCl (4×200 ml)
  6. washThe combined ether layers are washed with saturated aqueous sodium bicarbonate (100 ml) and saturated brine (150 ml)
  7. dry with materialThe ether solution is dried over sodium sulfate
  8. customthe solvent is removed
  9. customto give a brown oil which
  10. customcrystallizes
  11. customThe product is purified by preparative HPLC (4/1 hexanes/ether)

Sources & evidence

ORD record
ord-790c2e9754f74f2e85f401020e1089da
Source dataset
uspto-grants-1984_04
Patent number
US04440779

Reaction notes

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