반응 #159459

반응 방정식

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

→

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

용매

acetic acid

반응 조건

후처리

1. 1
   온도The mixture is cooled to room temperature
2. 2
   여과filtered through diatomaceous earth
3. 3
   농축the filtrate is concentrated under reduced pressure
4. 4
   기타The residue is partitioned between ethyl acetate and water
5. 5
   추출the aqueous phase is extracted with ethyl acetate
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   여과filtered
8. 8
   기타the filtrate is evaporated under reduced pressure
9. 9
   기타Purification by column chromatography
10. 10
    기타on silica gel, and further purification by preparative reverse-phase HPLC

실험 절차

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.

출처