Reacción #162227

Ecuación de reacción

HCl

6-bromohexahydro-2H-3,5-methanocyclopenta[b]furan-2-one

72a

6-bromohexahydro-2H-3,5-methanocyclopenta[b]furan-2-one

NaOH

→

6-oxonorbornane-2-carboxylic acid

Disolventes

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with Et2O
2. 2
   SecadoThe organic phase was dried (Na2SO4)
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated in vacuo
5. 5
   OtroThe resulting residue was purified by silica gel chromatography (0-20% MeOH/CH2Cl2 gradient)

Procedimiento

6-bromohexahydro-2H-3,5-methanocyclopenta[b]furan-2-one, 72a, (28.0 g, 129.0 mmol) was treated with NaOH (258.0 mL of 2 M solution, 516.0 mmol) in H2O (350 mL) for 2 hour at room temperature. The reaction mixture was acidified with conc. HCl, extracted with Et2O. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (0-20% MeOH/CH2Cl2 gradient) to provide 16 g of 6-oxonorbornane-2-carboxylic acid.

Fuente