Potassium Carbonate → HCID 21288084, compound

HRID 868212Notes

Reaction equation

HRID 868212 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[S:5][CH:6]=1.Cl.Cl[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][O:1][C:2]1[CH:3]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 13277908Methyl 4-hydroxythiophene-2-carboxylate

Product 1

HCID 21288084HCID 21288084, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

3.00 g (19.0 mmol) of methyl 4-hydroxy-2-thiophenecarboxylate, 3.11 g (19.0 mmol) of 2-chloromethylpyridine hydrochloride and 5.24 g (37.9 mmol) of potassium carbonate are heated under reflux in 60 ml of absolute 2-butanone for 10 hours under nitrogen. The mixture is then evaporated in vacuo and the residue is partitioned between methylene chloride and saturated sodium bicarbonate solution. The aqueous phase is extracted twice more with 100 ml of methylene chloride each time and the combined organic phases are dried over sodium sulfate/active charcoal, filtered and evaporated. The residue is digested with diisopropyl ether.

Workup

  1. customThe mixture is then evaporated in vacuo
  2. customthe residue is partitioned between methylene chloride and saturated sodium bicarbonate solution
  3. extractionThe aqueous phase is extracted twice more with 100 ml of methylene chloride each time
  4. dry with materialthe combined organic phases are dried over sodium sulfate/active charcoal
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-173754239b17438095e56780c90626e7
Source dataset
uspto-grants-1988_10
Patent number
US04778803

Reaction notes

Loading…