Reacción #1340617

ord-0b4b747d3b6e41f18987ed26d8727b03

Ecuación de reacción

COC(=O)c1ccc2nc(-c3ccccc3)oc2c1
methyl 2-phenyl-benzooxazole-6-carboxylate
[Li+].[OH-]
LiOH
O=C(O)c1ccc2nc(-c3ccccc3)oc2c1
2-Phenyl-benzooxazole-6-carboxylic acid
Cl
HCl
O=C(Cl)c1ccccc1
1t
O=C(Cl)c1ccccc1
benzoyl chloride

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    ExtracciónThe resulting mixture was extracted with EtOAc (2×)
  2. 2
    LavadoThe organic solution was washed with aq. NaCl
  3. 3
    Secadodried over Na2SO4
  4. 4
    Concentraciónconcentrated

Procedimiento

2-Phenyl-benzooxazole-6-carboxylic acid, 1v. A mixture of methyl 2-phenyl-benzooxazole-6-carboxylate 1u (0.37 g, 1.46 mmol) and LiOH (0.10 g, 4.2 mmol) in THF (4 mL), MeOH (4 mL), and H2O (4 mL) was stirred at room temperature for 6 h. Aqueous 1N HCl solution was added to the mixture to adjust pH to 3-4. The resulting mixture was extracted with EtOAc (2×). The organic solution was washed with aq. NaCl, dried over Na2SO4 and concentrated to give 1t (0.34 g).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08455476B2uspto-grants-2013_06