반응 #162227

반응 방정식

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

용매

H2O

반응 조건

후처리

1. 1
   추출extracted with Et2O
2. 2
   건조The organic phase was dried (Na2SO4)
3. 3
   여과filtered
4. 4
   농축concentrated in vacuo
5. 5
   기타The resulting residue was purified by silica gel chromatography (0-20% MeOH/CH2Cl2 gradient)

실험 절차

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.

출처