Water → Methyl (3-methoxy-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl)acetate

HRID 2076620Notes

Reaction equation

HRID 2076620 reaction equation
N1C=CC=CC=1.[F:7][C:8]([F:14])([F:13])[S:9]([OH:12])(=[O:11])=[O:10].O[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:18][C:17]=1[O:27][CH3:28].O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:28][O:27][C:17]1[CH:18]=[C:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH:20]=[CH:21][C:16]=1[O:10][S:9]([C:8]([F:14])([F:13])[F:7])(=[O:12])=[O:11]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 62406Trifluoromethanesulfonic acidHCID 85214Methyl 4-hydroxy-3-methoxyphenylacetate

Product 1

HCID 86617406Methyl (3-methoxy-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl)acetateYield 99.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Pyridine (2.10 ml, 25.9 mmol), anhydrous trifluoromethanesulfonic acid (1.61 ml, 9.53 mmol) and 4-dimethylaminopyridine (30 mg, 0.25 mmol) were added to a solution of methyl (4-hydroxy-3-methoxyphenyl)acetate (1.70 g, 8.66 mmol) in methylene chloride (20 ml) and the mixture was stirred under ice-cooling for 10 minutes and then stirred at room temperature for 20 minutes. After the reaction mixture was poured into water and the mixture was extracted with ethyl acetate, the organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=2/1) to give methyl (3-methoxy-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl)acetate (2.84 g, yield: 99%).

Workup

  1. temperaturecooling for 10 minutes
  2. stirringstirred at room temperature for 20 minutes
  3. extractionthe mixture was extracted with ethyl acetate
  4. washthe organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe residue obtained
  7. customby removing the solvent under reduced pressure
  8. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-72801ca5016047b8bc0b45013c1383e6
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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