HCID 11370798, compound → HCID 9865298, compound

HRID 1058984Notes

Reaction equation

HRID 1058984 reaction equation
[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=1)=[O:7]>C(O)(=O)C>[F:1][C:2]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[C:3](=[O:4])[CH:2]=[C:21]([CH3:20])[O:7][C:6]=1[C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

3

Reactant 1

HCID 11370798HCID 11370798, compound

Product 1

HCID 9865298HCID 9865298, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 2-(2,4-Difluorophenoxy)-1-(4-methanesulfonylphenyl)ethanone ( 4.60 g; 14 mmol) in acetic acid (70 ml), polyphosphoric acid (45 g) was added and then heated at 140° C. for 5 hours. After cooling, the reaction was poured into ice-water, extracted with ethyl acetate (2×100 ml), the organic solution dried (Na2SO4) and the solvent removed under reduced pressure. The residual oil was purified by column chromatography with silica gel and ethyl acetate/n-hexane (1:2) as eluent. Recrystallization from ethanol gave 3-(2,4-difluorophenoxy)-2-(4-methanesulfonylphenyl)-6-methylpyran-4-one (0.64 g), m.p. 191° C. (Compound 45 in Table 4).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (2×100 ml)
  3. dry with materialthe organic solution dried (Na2SO4)
  4. customthe solvent removed under reduced pressure
  5. customThe residual oil was purified by column chromatography with silica gel and ethyl acetate/n-hexane (1:2) as eluent
  6. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-799ace42354d425094067023032e5480
Source dataset
uspto-grants-2003_02
Patent number
US06518303B2

Reaction notes

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