Water → ethyl 7-(2,5-dimethylphenoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 855134Notes

Reaction equation

HRID 855134 reaction equation
F[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:8]([C:12]([F:15])([F:14])[F:13])[O:9]2)=[CH:4][CH:3]=1.[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=1[OH:29].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.CCOCC>[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=1[O:29][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:8]([C:12]([F:15])([F:14])[F:13])[O:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 72672,5-DimethylphenolHCID 11430Potassium CarbonateHCID 58934808ethyl 7-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 69519100ethyl 7-(2,5-dimethylphenoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To 0.200 g (0.689 mmole) of ethyl 7-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylate in 2.5 mL of DMF was added 0.118 g (0.946 mmol) of 2,5-dimethyl phenol to the vessel followed by 0.131 g (0.946 mmole) of potassium carbonate. The suspension was prepared in a capped vial and placed in a J-KEM heating block equipped with shaker, condenser and nitrogen atmosphere. The block was heated to 110° C. for 20hrs. For work up, 10 mL of H2O and 5 mL of ether was added to the mixture. The organic layer was separated and then the aqueous was extracted 3 times with ether. The product was then run through a pre-packed silica gel plug (20 mL, 5 g capacity) and the silica column washed with 4×5 mL aliquots of ether. Concentration of the solution afforded the product with was used directly in the next step without further purification.

Workup

  1. customThe suspension was prepared in a capped vial and
  2. customequipped with shaker, condenser and nitrogen atmosphere
  3. customThe organic layer was separated
  4. extractionthe aqueous was extracted 3 times with ether
  5. washthe silica column washed with 4×5 mL aliquots of ether
  6. customConcentration of the solution afforded the product
  7. customwith was used directly in the next step without further purification

Sources & evidence

ORD record
ord-d1de590a92494864840d818b01c13910
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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