Reacción #159459

Ecuación de reacción

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

→

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

Disolventes

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture is cooled to room temperature
2. 2
   Filtraciónfiltered through diatomaceous earth
3. 3
   Concentraciónthe filtrate is concentrated under reduced pressure
4. 4
   OtroThe residue is partitioned between ethyl acetate and water
5. 5
   Extracciónthe aqueous phase is extracted with ethyl acetate
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Otrothe filtrate is evaporated under reduced pressure
9. 9
   OtroPurification by column chromatography
10. 10
    Otroon silica gel, and further purification by preparative reverse-phase HPLC

Procedimiento

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.

Fuente