تفاعل #159459

معادلة التفاعل

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

→

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

المذيبات

acetic acid

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture is cooled to room temperature
2. 2
   ترشيحfiltered through diatomaceous earth
3. 3
   تركيزthe filtrate is concentrated under reduced pressure
4. 4
   أخرىThe residue is partitioned between ethyl acetate and water
5. 5
   استخلاصthe aqueous phase is extracted with ethyl acetate
6. 6
   تجفيفdried over anhydrous magnesium sulfate
7. 7
   ترشيحfiltered
8. 8
   أخرىthe filtrate is evaporated under reduced pressure
9. 9
   أخرىPurification by column chromatography
10. 10
    أخرىon silica gel, and further purification by preparative reverse-phase HPLC

الإجراء التجريبي

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.

المصدر