Reacción #1869217

ord-568c9d6a32e34e1fa7c3768c361c2f53

Ecuación de reacción

[Al+3].[Cl-].[Cl-].[Cl-]
AlCl3
COc1cc(C(C)(C)C)ccc1S(=O)(=O)Cl
4-tert-butyl-2-methoxybenzenesulfonyl chloride
C1CCNC1
pyrrolidine
O=S(=O)(c1ccccc1O)N1CCCC1
subtitle compound
Rendimiento 53.3%
O=S(=O)(c1ccccc1O)N1CCCC1
2-(pyrrolidin-1-ylsulfonyl)phenol
Rendimiento 53.3%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Concentraciónconcentrated in vacuo
  2. 2
    workup.DISSOLUTIONThe residue was dissolved in xylene (10 ml)
  3. 3
    workup.STIRRINGThe resulting mixture was stirred for 18 h at 70° C
  4. 4
    workup.ADDITIONwas poured
  5. 5
    workup.STIRRINGinto stirred ice-cold water
  6. 6
    Extracciónextracted with ether (2×30 ml)
  7. 7
    SecadoThe ether layer was dried over sodium sulfate
  8. 8
    Filtraciónfiltered
  9. 9
    Concentraciónconcentrated

Procedimiento

To a solution of 4-tert-butyl-2-methoxybenzenesulfonyl chloride (258 mg, 0.99 mmol) in DMF (6 ml) was added pyrrolidine (70 mg, 0.99 mmol) and the solution was stirred at ambient temperature for 30 minutes, and concentrated in vacuo. The residue was dissolved in xylene (10 ml) and then added to mixture of AlCl3 (525 mg, 3.39 mmol) in xylene (5 ml). The resulting mixture was stirred for 18 h at 70° C. After colling the mixture was poured into stirred ice-cold water, and extracted with ether (2×30 ml). The ether layer was dried over sodium sulfate, filtered and concentrated to give 120 mg of subtitle compound.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07498338B2uspto-grants-2009_03