Reacción #1519

ord-436174135cd54d56bccd8e2f39d9c63d

Ecuación de reacción

CCCCCCCCCCOc1ccc(OC(=O)C2CCc3cc(OCc4ccccc4)ccc3C2)cc1
2-(4-decyloxyphenyloxycarbonyl)-1,2,3,4-tetrahydro-6-benzyloxynaphthalene
[H][H]
hydrogen
CCCCCCCCCCOc1ccc(OC(=O)C2CCc3cc(O)ccc3C2)cc1
2-(4-decyloxyphenyloxycarbonyl)-1,2,3,4-tetrahydro-6-hydroxynaphthalene
Rendimiento 97.7%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otro5% palladium/carbon was removed
  2. 2
    Concentraciónthe filtrate was concentrated
  3. 3
    OtroThe concentrate obtained
  4. 4
    Otrowas purified by column chromatography
  5. 5
    Otroto obtain

Procedimiento

Then, 0.04 g of 5% palladium/carbon and 10 ml of a tetrahydrofuran solution containing 0.36 g of 2-(4-decyloxyphenyloxycarbonyl)-1,2,3,4-tetrahydro-6-benzyloxynaphthalene were stirred overnight at room temperature in a stream of hydrogen to decompose a benzyl protective group by hydrogenation. 5% palladium/carbon was removed using Celite as a filter aid, and the filtrate was concentrated. The concentrate obtained was purified by column chromatography to obtain 0.29 g of 2-(4-decyloxyphenyloxycarbonyl)-1,2,3,4-tetrahydro-6-hydroxynaphthalene as a white crystal (isolated yield: 97%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05725798uspto-grants-1998_03