Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (2R)-1-(2,4-difluorophenyl)-2-hydroxypropan-1-one

HRID 1654197Notes

Reaction equation

HRID 1654197 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:19])[C@H:10]([O:12]C1CCCCO1)[CH3:11].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:19])[C@H:10]([OH:12])[CH3:11]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10199305(2R)-1-(2,4-difluorophenyl)-2-((tetrahydro-2H-pyran-2-yl)oxy)propan-1-one

Product 1

HCID 9794084(2R)-1-(2,4-difluorophenyl)-2-hydroxypropan-1-oneYield 74.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

In ethanol (3 ml) was dissolved (2R)-2',4'-difluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone (121 mg), to which was added pyridinium p-toluenesulfonate (25 mg), and the mixture was stirred for one hour at 55° C. The solvent was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate (20 ml). The solution was washed with water and dried over anhydrous magnesium sulfate, followed by distilling off the solvent. The residue was purified by means of a silica gel chromatography (eluent: hexane-ethyl acetate=5:1) to give (2R)-2',4'-difluoro-2-hydroxypropiophenone (62 mg) as a pale yellow oily product. [α]D +68.7 (c=1.8 in chloroform)

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (20 ml)
  3. washThe solution was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationby distilling off the solvent
  6. customThe residue was purified by means of a silica gel chromatography (eluent: hexane-ethyl acetate=5:1)

Sources & evidence

ORD record
ord-148157f537fd4a35bacc4db27fa6b91b
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

Loading…