Phenol → HCID 68615701, compound

HRID 229742Notes

Reaction equation

HRID 229742 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[O:9][C:8]([C:14]([O-:16])=[O:15])=[C:7]([C:17]1[S:18][CH:19]=[C:20]([CH3:22])[N:21]=1)[C:6]2=[O:23])[CH3:2].[C:24]1(O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl.C(OCC)(=O)C>[C:24]1([O:15][C:14]([C:8]2[O:9][C:10]3[C:5]([C:6](=[O:23])[C:7]=2[C:17]2[S:18][CH:19]=[C:20]([CH3:22])[N:21]=2)=[CH:4][C:3]([CH2:1][CH3:2])=[C:12]([OH:13])[CH:11]=3)=[O:16])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 996PhenolHCID 178435412HCID 178435412, compound

Product 1

HCID 68615701HCID 68615701, compoundYield 40.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 5 mL Schlenk tube 18 mg (0.054 mmol) 6-ethyl-7-hydroxy-3-[(4-methyl)-1,3-thiazol-2-yl]-4-oxo-4H-chromene-2-carboxylate 10 (Aldrich, no. R66,464-2) were suspended in 0.5 mL methylene chloride. Then 51 mg (0.54 mmol) phenol and 18 μl (0.108 mmol) triflate anhydride were added at ambient temperature. The resulting mixture was stirred for 20 hours, diluted in 10 mL of ethyl acetate and washed with water and saturated solutions of sodium bicarbonate and sodium chloride. The organic layer was separated, dried over magnesium sulfate and filtered. Evaporation of the solvent on a rotavapor yielded 9 mg of a yellow solid. This crude product was used without further purification.

Workup

  1. washwashed with water and saturated solutions of sodium bicarbonate and sodium chloride
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customEvaporation of the solvent on a rotavapor

Sources & evidence

ORD record
ord-f4f07285a73748ddb674bb6368412db5
Source dataset
uspto-grants-2009_07
Patent number
US07563902B2

Reaction notes

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