反应 #162227

反应方程式

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

溶剂

H2O

反应条件

后处理

1. 1
   萃取extracted with Et2O
2. 2
   干燥The organic phase was dried (Na2SO4)
3. 3
   过滤filtered
4. 4
   浓缩concentrated in vacuo
5. 5
   其他The resulting residue was purified by silica gel chromatography (0-20% MeOH/CH2Cl2 gradient)

实验过程

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.

来源