Potassium Carbonate → HCID 14695585, compound

HRID 703694Notes

Reaction equation

HRID 703694 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9]C(OC)=O)=[CH:4][C:3]=1[N:14]1[C:18](=[O:19])[C:17](=[C:20]([CH3:22])[CH3:21])[O:16][C:15]1=[O:23].C(=O)([O-])[O-].[K+].[K+]>CO>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:14]1[C:18](=[O:19])[C:17](=[C:20]([CH3:21])[CH3:22])[O:16][C:15]1=[O:23]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 14695618HCID 14695618, compound

Product 1

HCID 14695585HCID 14695585, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a dried methanol solution (100 ml) of 3-(2'-fluoro-4'-chloro-5'-methoxycarbonyloxyphenyl)-5-isopropylidene-1,3-oxazolidine-2,4-dione (3.44 g, 10 mmol), which was synthesized by a method shown in Reference Example 12 described below, was added potassium carbonate (1.38 g, 10 mmol) and the mixture was heated at reflux for 2 hours. After the reaction was completed, the resulting mixture was quenched with an aqueous solution of ammonium chloride and extracted with ether. The ethereal extracts were dried and evaporated as small a volume as possible. The resulting residue was purified by silica gel column chromatography to give pure 3-(2'-fluoro-4'-chloro-5'-hydroxyphenyl)-5-isopropylidene-1,3-oxazolidine-2,4-dione (1.60 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. customthe resulting mixture was quenched with an aqueous solution of ammonium chloride
  4. extractionextracted with ether
  5. customThe ethereal extracts were dried
  6. customevaporated as small a volume as possible
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e94c9605e16e4b83a453c5de6aa72ab5
Source dataset
uspto-grants-1991_01
Patent number
US04983751

Reaction notes

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