Reacción #1354128

ord-fa2c7b0be44b4d69909bbd8d7c65606c

Ecuación de reacción

COc1cc(S(=O)(=O)[O-])ccc1OS(=O)(=O)c1ccc(C)cc1.[Na+]
sodium 3-methoxy-4-(4′-methylphenylsulfonyloxy)-benzenesulfonate
[Cl-].c1ccc([S+](c2ccccc2)c2ccccc2)cc1
triphenylsulfonium chloride
COc1cc(S(=O)(=O)[O-])ccc1OS(=O)(=O)c1ccc(C)cc1.c1ccc([S+](c2ccccc2)c2ccccc2)cc1
triphenylsulfonium 3-methoxy-4-(4′-methylphenyl-sulfonyloxy)benzenesulfonate
Rendimiento 56.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe organic layer was separated
  2. 2
    Lavadowashed with 400 g of water
  3. 3
    Concentraciónconcentrated in vacuum
  4. 4
    OtroThe residue, 150 g, was purified by silica gel column chromatography (eluent, dichloromethane/methanol)

Procedimiento

The sodium 3-methoxy-4-(4′-methylphenylsulfonyloxy)-benzenesulfonate crude product obtained in Synthesis Example 1, 90 g, was added to the aqueous triphenylsulfonium chloride solution obtained in Synthesis Example 2 and 400 g of dichloromethane, which was stirred for one hour at room temperature. The organic layer was separated, washed with 400 g of water, and concentrated in vacuum. The residue, 150 g, was purified by silica gel column chromatography (eluent, dichloromethane/methanol), obtaining the end product, triphenylsulfonium 3-methoxy-4-(4′-methylphenyl-sulfonyloxy)benzenesulfonate as an oily matter in an amount of 69 g (yield 56%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06551758B2uspto-grants-2003_04