反応 #162227

反応方程式

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

溶媒

H2O

反応条件

後処理

1. 1
   抽出extracted with Et2O
2. 2
   乾燥The organic phase was dried (Na2SO4)
3. 3
   ろ過filtered
4. 4
   濃縮concentrated in vacuo
5. 5
   その他The resulting residue was purified by silica gel chromatography (0-20% MeOH/CH2Cl2 gradient)

実験手順

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.

出典