反应详情

The cinnamic ester (1) (5.0 g, 14.8 mmol) was dissolved in 100 mL of acetic acid and 7.6 g (17.2 mmol) of lead tetracetate was added. After allowing the mixture to stir for one hour at room temperature, the solvent was removed. Toluene (100 mL) was added and the slurry concentrated, then 100 mL of chloroform (CHCl3) was added, the solid broken up thoroughly, and the solution decanted. Chloroform (100 mL) was added to the solid and the mixture refluxed briefly, filtered, and the filtrate combined with the previous CHCl3 solution. After concentrating the organic solution the residue was chromatographed on 350 g of silica gel eluting with 1:19 (v/v) acetone:CHCl3. Fractions 83-140 (15 mL/fraction) were combined and concentrated to yield the product which was crystallized from CH2Cl2 (3.45 g, 72%), m.p. 113°-114° C.

1. customthe solvent was removed
2. additionToluene (100 mL) was added
3. concentrationthe slurry concentrated
4. addition100 mL of chloroform (CHCl3) was added
5. customdecanted
6. additionChloroform (100 mL) was added to the solid
7. temperaturethe mixture refluxed briefly
8. filtrationfiltered
9. concentrationAfter concentrating the organic solution the residue
10. customwas chromatographed on 350 g of silica gel eluting with 1:19 (v/v) acetone
11. concentrationconcentrated
12. customto yield the product which
13. customwas crystallized from CH2Cl2 (3.45 g, 72%), m.p. 113°-114° C.