Reaktion #159459

Reaktionsgleichung

3-chloro-1-methoxybicyclo[3.2.2]non-6-en-2,4-dione

→

1-methoxybicyclo[3.2.2]non-6-en-2,4-dione

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is cooled to room temperature
2. 2
   Filtrationfiltered through diatomaceous earth
3. 3
   Einengenthe filtrate is concentrated under reduced pressure
4. 4
   SonstigeThe residue is partitioned between ethyl acetate and water
5. 5
   Extraktionthe aqueous phase is extracted with ethyl acetate
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Sonstigethe filtrate is evaporated under reduced pressure
9. 9
   SonstigePurification by column chromatography
10. 10
    Sonstigeon silica gel, and further purification by preparative reverse-phase HPLC

Vorschrift

Zinc dust (1.53 g, 0.0233 mol) is added in one portion to a solution of 3-chloro-1-methoxybicyclo[3.2.2]non-6-en-2,4-dione, prepared in Step 1b, in glacial acetic acid (20 ml) and the mixture is heated to 95° C. for 1¾ hours. The mixture is cooled to room temperature, filtered through diatomaceous earth and the filtrate is concentrated under reduced pressure. The residue is partitioned between ethyl acetate and water, and the aqueous phase is extracted with ethyl acetate. The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. Purification by column chromatography on silica gel, and further purification by preparative reverse-phase HPLC, gives 1-methoxybicyclo[3.2.2]non-6-en-2,4-dione.

Quelle