Diethyl Ether → HCID 86587321, compound

HRID 352263Notes

Reaction equation

HRID 352263 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([OH:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1[C:12]1[C:13]([NH:15][C:16](=[O:18])[CH:17]=1)=[O:14].[CH:19]([O:21][CH2:22][CH3:23])=[CH2:20].C1(C)C=CC(S(O)(=O)=O)=CC=1.CCOCC>C(Cl)Cl.N1C=CC=CC=1>[CH2:19]([O:21][CH:22]([O:9][C:6]1[C:5]([F:10])=[C:4]([F:11])[C:3]([C:12]2[C:13]([NH:15][C:16](=[O:18])[CH:17]=2)=[O:14])=[C:2]([F:1])[C:7]=1[F:8])[CH3:23])[CH3:20]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 8023Ethyl vinyl etherHCID 86587319HCID 86587319, compound

Product 1

HCID 86587321HCID 86587321, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3 g of the 2,3,5,6-tetrafluoro-4-hydroxyphenylmaleimide obtained in Example 2 was dissolved in 20 ml of methylene chloride. Thereto was added 2.1 g of ethyl vinyl ether and 58 mg of pyridine salt of p-toluenesulfonic acid. The mixture was stirred at room temperature for 12 hours. 100 ml of ether was added. The mixture was washed with an aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent to obtain 2.8 g of an intended compound (yield: 73%).

Workup

  1. washThe mixture was washed with an aqueous sodium chloride solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. distillationThe resulting solution was subjected to vacuum distillation
  4. customto remove the solvent

Sources & evidence

ORD record
ord-0dbcf7d3d1474ffd81dd4514dda97beb
Source dataset
uspto-grants-2004_06
Patent number
US06746722B2

Reaction notes

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