Potassium Carbonate → HCID 20464780, compound

HRID 325432Notes

Reaction equation

HRID 325432 reaction equation
Cl.[NH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].O=[C:10]([CH2:16][C:17](=O)[CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+].[Na]>O.CCOCC.C1C=CC=CC=1>[CH3:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[O:19][CH2:18][C:17]1[CH:16]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:2][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 5360545SodiumHCID 20464714HCID 20464714, compound

Product 1

HCID 20464780HCID 20464780, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
5 °C

Procedure

To a stirred, refluxing mixture of ethyl glycinate hydrochloride (100 g, 0.71 m), ethyl 2,4-dioxo-5-(3-methylphenoxy)pentanoate (187 g, 0.71 m) and benzene (650 ml) under a nitrogen atmosphere is added finely powdered anhydrous potassium carbonate (50 g, 0.36 m) in five portions over one hour, the eliminated water being collected in a Dean-Stark trap until the theoretical amount (12.6 ml) is collected. The mixture is cooled to 5° C., then 750 ml dry ethanol is added and sodium metal (16.5 g, 0.71 mol) is added in small pieces at a rate which permits the internal reaction temperature to be maintained at less than 40° with cooling. Stirring is continued in the ice bath for an additional 1/2 hour, and the reaction mixture is then poured into a 5-liter separatory funnel containing ether (1 liter) and water (2 liters). The layers are separated and the aqueous layer is re-extracted with ether. The combined ether layers are washed with water and saturated brine. The organic layer is dried over sodium sulfate and concentrated to give a residue which is purified by preparative HPLC to afford diethyl 4-(3-methylphenoxy)methylpyrrole-2,5-dicarboxylate.

Workup

  1. temperatureTo a stirred, refluxing
  2. customthe eliminated water being collected in a Dean-Stark trap until the theoretical amount (12.6 ml)
  3. customis collected
  4. addition750 ml dry ethanol is added
  5. temperatureto be maintained at less than 40°
  6. temperaturewith cooling
  7. additionthe reaction mixture is then poured into a 5-liter separatory funnel
  8. customThe layers are separated
  9. extractionthe aqueous layer is re-extracted with ether
  10. washThe combined ether layers are washed with water and saturated brine
  11. dry with materialThe organic layer is dried over sodium sulfate
  12. concentrationconcentrated
  13. customto give a residue which
  14. customis purified by preparative HPLC

Sources & evidence

ORD record
ord-b7c107313ff3422caa85c2a52e379dcd
Source dataset
uspto-grants-1984_04
Patent number
US04440779

Reaction notes

Loading…