Réaction #1552056

ord-f425b498168f4341b45de38d74c006ef

Équation de réaction

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

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

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

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08999623B2uspto-grants-2015_04