تفاعل #162227

معادلة التفاعل

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

المذيبات

H2O

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with Et2O
2. 2
   تجفيفThe organic phase was dried (Na2SO4)
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated in vacuo
5. 5
   أخرىThe resulting residue was purified by silica gel chromatography (0-20% MeOH/CH2Cl2 gradient)

الإجراء التجريبي

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.

المصدر