2-(4-Fluorophenyl)-1-(4-(methylsulfonyl)phenyl)ethanone → HCID 9841715, compound

HRID 1058983Notes

Reaction equation

HRID 1058983 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1>C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9](=[O:10])[CH:8]=[C:5]([CH3:4])[O:10][C:9]=2[C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 111970952-(4-Fluorophenyl)-1-(4-(methylsulfonyl)phenyl)ethanone

Product 1

HCID 9841715HCID 9841715, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 2-(4-fluorophenyl)-1-(4-methanesulfonylphenyl)ethanone (1 g; 3.4 moles) in glacial acetic acid (15 ml), polyphosphoric acid (10 g) was added and then heated at 140° C. for 16 hours. After cooling, the reaction was poured into ice-water, extracted with ethyl acetate (2×50 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 as eluent. 3-(4-fluorophenyl)-2-(4-methanesulfonylphenyl)-6-methylpyran-4-one was obtained (0.5 g) m.p. 237° C. (Compound 2 in Table 4).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (2×50 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 as eluent

Sources & evidence

ORD record
ord-b9456205aadf42bc9d659bc8928f084f
Source dataset
uspto-grants-2003_02
Patent number
US06518303B2

Reaction notes

Loading…