Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (1R)-1-[2-(2,4-difluorophenyl)-2-oxiranyl]ethanol

HRID 2395190Notes

Reaction equation

HRID 2395190 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C@H:12]([O:14]C2CCCCO2)[CH3:13])[CH2:11][O:10]1.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]1([C@H:12]([OH:14])[CH3:13])[CH2:11][O:10]1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 542112042H-Pyran, 2-[(1R)-1-[2-(2,4-difluorophenyl)oxiranyl]ethoxy]tetrahydro-

Product 1

HCID 15130436(1R)-1-[2-(2,4-difluorophenyl)-2-oxiranyl]ethanolYield 54.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 600 ml of ethanol were dissolved 82 g of 2-(2,4-difluorophenyl)-2-[(1R)-1-(3,4,5,6-tetrahydro-2H-pyran-2-yl)oxyethyl]oxirane (prepared by a method disclosed in Japanese Patent Application Laid-open No. 74168/1992, JP-A-4-74168) and 6.3 g of pyridinium p-toluenesulfonate, and the solution was stirred at 55° C. for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in 1 liter of ethyl acetate, and washed twice, each time with 200 ml of water. The aqueous phase was extracted twice, each time with 100 ml of ethyl acetate. The organic phases were collected, washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified with using silica gel chromatography (gradient eluent; hexane:ethyl acetate=10:1→8:1→3:1) to give 31.5 g of (1R)-1-[2-(2,4-difluorophenyl)-2-oxiranyl]ethanol as a pale yellow oil.

Workup

  1. customprepared by a method
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 1 liter of ethyl acetate
  4. washwashed twice
  5. extractionThe aqueous phase was extracted twice
  6. customThe organic phases were collected
  7. washwashed with saturated aqueous solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue was purified with using silica gel chromatography (gradient eluent; hexane:ethyl acetate=10:1→8:1→3:1)

Sources & evidence

ORD record
ord-5b55d080cc674f6d98052c82d94ffc5b
Source dataset
uspto-grants-1998_09
Patent number
US05814324

Reaction notes

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