Reacción #417919

ord-2898d3da41d54f45b6bad8cd42ec1dc8

Ecuación de reacción

[O]=[Cr](=[O])([O-])[Cl].c1cc[nH+]cc1
PCC
CCCCCC/C=C\CCCOc1cccc(CO)c1
alcohol
CCCCCC/C=C\CCCOc1cccc(CO)c1
3-(undec-4Z-enyloxy)benzyl alcohol
CCCCCC/C=C\CCCOc1cccc(C=O)c1
yellow oil
Rendimiento 99.1%
CCCCCC/C=C\CCCOc1cccc(C=O)c1
3-(undec-4Z-enyloxy)benzaldehyde
Rendimiento 99.1%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Secadodried by coevaporation with toluene
  2. 2
    TemperaturaThe reaction is heated to the reflux point of the DCM for 1 hour
  3. 3
    TemperaturaAfter cooling
  4. 4
    workup.ADDITIONthe reaction medium is diluted with ether
  5. 5
    Filtraciónfiltered through Florisil
  6. 6
    ConcentraciónAfter concentrating

Procedimiento

10 mL of anhydrous DCM and then 190 mg of PCC (881 μmol) are added under argon to 120 mg of alcohol 16 (434 μmol) dried by coevaporation with toluene. The reaction is heated to the reflux point of the DCM for 1 hour. After cooling, the reaction medium is diluted with ether and filtered through Florisil. After concentrating, 118 mg of a yellow oil are obtained, i.e. a yield of 99%.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08877684B2uspto-grants-2014_11