Reaction #84048

Reaction equation

quinuclidin-3-one hydrochloride

sodium methoxide

→

title compound

Quinuclidin-3-one

Solvents

methanol

methanol

Conditions

Workup

1. 1
   FiltrationThe resulting precipitate is filtered off with suction
2. 2
   Concentrationthe filtrate is concentrated in vacuo
3. 3
   OtherThe residue is partitioned between chloroform and water
4. 4
   Extractionextracted with chloroform
5. 5
   DryingThe combined organic phases are dried over sodium sulfate
6. 6
   Concentrationconcentrated in vacuo

Procedure

100 g (0.62 mol) of quinuclidin-3-one hydrochloride are suspended in 2 l of methanol. At 0° C., a solution of 33.4 g (0.62 mol) of sodium methoxide in 250 ml of methanol is slowly added dropwise. The mixture is stirred at room temperature for 16 h. The resulting precipitate is filtered off with suction, and the filtrate is concentrated in vacuo. The residue is partitioned between chloroform and water and extracted with chloroform. The combined organic phases are dried over sodium sulfate and concentrated in vacuo. 58.8 g (75.9% of theory) of the title compound are obtained.

Source