Ethyl Acetate → HCID 10808954, compound

HRID 1031674Notes

Reaction equation

HRID 1031674 reaction equation
[F:1][C:2]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:16]=[CH:15][C:8]([O:9][C:10](=[CH2:14])C(O)=O)=[CH:7][C:6]=1[NH:17][S:18]([CH3:21])(=[O:20])=[O:19].[C:27](OCC)(=[O:29])C>>[F:1][C:2]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[C:6]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[CH:7][C:8]2[O:9][CH:10]=[CH:14][C:27](=[O:29])[C:15]=2[CH:16]=1

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 86744199HCID 86744199, compound

Product 1

HCID 10808954HCID 10808954, compoundYield 42%

Procedure

30 g of polyphosphoric acid was added to 1.0 g of trans-3-[4-(2,4-difluorophenoxy)-3-methylsulfonylaminophenoxylacrylic acid. The mixture was stirred for 1 hour at 55°-65° C. The reaction mixture was introduced into 200 ml of ice water. 50 ml of ethyl acetate was added thereto. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: a 5 : 1 mixture of toluene and ethyl acetate) to obtain 0.4 g (yield: 42.0%) of 6-(2,4-difluorophenoxy)-7-methylsulfonylamino-4H-1-benzopyran-4-one. Melting point: 182.2°-182.8° C. (recrystallized from ethyl acetate)

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materiala saturated aqueous sodium chloride solution in this order, and dried with anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue was purified by a column chromatography (eluant
  6. additiona 5 : 1 mixture of toluene and ethyl acetate)

Sources & evidence

ORD record
ord-347ae6e1b7c5470abb6a12f2620e290f
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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