Réaction #312536

Équation de réaction

4-bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one

tetrahydrofuran

→

4-hydroxy-2-(6-carboxyhexyl)cyclopent-2-en-1-one

Solvants

water

water

ether

Conditions de réaction

Traitement

1. 1
   Filtrationfiltered
2. 2
   Extractionextracted with additional ether
3. 3
   LavageThe combined organic phases are washed successively with water and saturated sodium chloride solution
4. 4
   Séchagedried over magnesium sulfate
5. 5
   Concentrationconcentrated

Mode opératoire

To a stirred solution of 56.0 g. of crude 4-bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one (Example 8) in 400 ml. of tetrahydrofuran and 133 ml. of water at 3° C. is added 44.1 g. (0.226 moles) of silver fluoborate during 25 minutes. The mixture is stirred at 0°-5° C. for 60 minutes, diluted with water and ether, and filtered. The aqueous portion of the filtrate is saturated with solid sodium chloride and extracted with additional ether. The combined organic phases are washed successively with water and saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. Column chromatography of the residue gives the subject compound as a mixture with 4-hydroxy-2-(6-carboxyhexyl)cyclopent-2-en-1-one, NMR(CDCl3) 3.60 (multiplet, O-methylene hydrogens) and 4.60 (multiplet, O-methine hydrogen).

Source