Ethanol → HCID 20464782, compound

HRID 325414Notes

Reaction equation

HRID 325414 reaction equation
Cl[C:2]([C:4]1[N:8]([CH3:9])[C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][C:5]=1[CH3:16])=[O:3].N1C=CC=CC=1.[CH2:23]([OH:25])[CH3:24]>C(Cl)Cl.CCOCC.CCOCC>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][C:7]1[N:8]([CH3:9])[C:4]([C:2]([O:25][CH2:23][CH3:24])=[O:3])=[C:5]([CH3:16])[CH:6]=1)[CH3:15]

Participants

6

Reactant 3

HCID 702EthanolHCID 1049PyridineHCID 20464712Ethyl [5-(chlorocarbonyl)-1,4-dimethyl-1H-pyrrol-2-yl]acetate

Product 1

HCID 20464782HCID 20464782, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

Ethyl 5-chlorocarbonyl-1,4 dimethylpyrrole-2-acetate (29.3 g, 0.12 mol, prepared acc. to U.S. Pat. No. 3,950,355) is dissolved in 150 ml of 1:1 methylene chloride/ether and added over 10 minutes to a solution of pyridine (15 ml) and absolute ethanol (20 ml) in ether (100 ml) with stirring. After addition is complete, 4-N,N-dimethylaminopyridine (300 mg) is added. Stirring is continued for three hours. Ether (250 ml) is then added and deposited solids are removed by filtration. The organic solution is washed with aqueous 1 N HCl (2×100 ml), then brine (100 ml), and the ether layer is dried with magnesium sulfate. The solvent is then removed to give 26.3 g (87%) of ethyl-1,4 dimethyl-5-ethoxycarbonylpyrrole-2-acetate as a low melting red solid.

Workup

  1. additionAfter addition
  2. stirringStirring
  3. customare removed by filtration
  4. washThe organic solution is washed with aqueous 1 N HCl (2×100 ml)
  5. dry with materialbrine (100 ml), and the ether layer is dried with magnesium sulfate
  6. customThe solvent is then removed

Sources & evidence

ORD record
ord-b3c450f12ec243c695b69eb3665d391a
Source dataset
uspto-grants-1984_04
Patent number
US04440779

Reaction notes

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