Reacción #1552056

ord-f425b498168f4341b45de38d74c006ef

Ecuación de reacción

C=CCOc1ccc([N+](=O)[O-])c(CO)c1
5-allyloxy-2-nitrobenzyl alcohol
O=C(OO)c1cccc(Cl)c1
m-chloroperoxybenzoic acid
O=[N+]([O-])c1ccc(OCC2CO2)cc1CO
5-glycidyloxy-2-nitrobenzyl alcohol

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otropeaks disappeared from the 1H-NMR spectrum (approximately 48 hours)
  2. 2
    LavadoThe reaction was then washed with aqueous sodium carbonate twice
  3. 3
    Secadowater three times and then dried over sodium sulfate
  4. 4
    OtroThe solvent was partially removed by rotary evaporation
  5. 5
    workup.ADDITIONpoured into hexanes
  6. 6
    Otroto precipitate the product
  7. 7
    FiltraciónThe resulting solid was collected by suction filtration
  8. 8
    Otrowas used in the next step without further purification

Procedimiento

5-allyloxy-2-nitrobenzyl alcohol (7.3 g, 35 mmol) and m-chloroperoxybenzoic acid (77 wt. %, 9.4 g, 42 mmol) were dissolved in dichloromethane and refluxed until the allyl peaks disappeared from the 1H-NMR spectrum (approximately 48 hours). The reaction was then washed with aqueous sodium carbonate twice, water three times and then dried over sodium sulfate. The solvent was partially removed by rotary evaporation and then poured into hexanes to precipitate the product. The resulting solid was collected by suction filtration and was used in the next step without further purification.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08999623B2uspto-grants-2015_04