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

HRID 1491734Notes

Reaction equation

HRID 1491734 reaction equation
O1CCCCC1[O:7][C@@H:8]([C:10]1([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[F:20])[CH2:12][O:11]1)[CH3:9].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[F:20][C:14]1[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]=1[C:10]1([C@H:8]([OH:7])[CH3:9])[CH2:12][O:11]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]ethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

2-[(1R)-1-(3,4,5,6-Tetrahydro-2H-pyran-2-yl)oxyethyl]-2-(2,4-difluorophenyl)oxirane (82 g; manufactured by a method disclosed in Japanese Laid Open Application Hei 04/074168-A) and 6.3 g of pyridinium p-toluenesulfonate were dissolved in 600 ml of ethanol and the solution was stirred at 55° C. for 1 hour. The reaction solution was concentrated under reduced pressure. The residue was dissolved in 1 liter of ethyl acetate and the resulting solution was washed with water (2×200 ml). The aqueous layer was extracted with ethyl acetate (2×100 ml). The organic layers were combined, washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate and distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluate; hexane:ethyl acetate=10:1 to 8:1 to 3:1) to give 31.5 g of (1R)-1-[2-(2,4-difluorophenyl)-2-oxiranyl]ethanol as a pale yellow oil.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 1 liter of ethyl acetate
  3. washthe resulting solution was washed with water (2×200 ml)
  4. extractionThe aqueous layer was extracted with ethyl acetate (2×100 ml)
  5. washwashed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. distillationdistilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography (eluate; hexane:ethyl acetate=10:1 to 8:1 to 3:1)

Sources & evidence

ORD record
ord-baaa344d79014307b846bcec5c3c1d59
Source dataset
uspto-grants-1994_12
Patent number
US05371101

Reaction notes

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