HCID 13298918, compound → ANGELICIN,6-METHYL

Participants

Reaction Steps

The 6-methyl-7-hydroxy-8-allylcoumarin (VII) (1.7 g) was dissolved in EtOAc (150 ml) and into the solution, cooled in an ice bath, a stream of ozonized oxigen was bubbled until 1.1 times the stoichiometric amount of ozone was reached. The solution was then immediately submitted to hydrogenation in the presence of Pd 10% on CaCO3 (0.3 g) and the mixture stirred until the rapid absorption of hydrogen ceased. The catalyst was removed by filtration, the solvent evaporated at reduced pressure, and the residue treated with 85% H3PO4 (60 ml). The reaction mixture was then placed into a thermostatic bath at 100° C. for 20 min, chilled, diluted with H2O (200 ml) and extracted with CHCl3. From the dried (Na2SO4) organic phase the solvent was evaporated under reduced pressure and the residue chromatographed on a silica gel column by eluting with CHCl3, yielding the 6-methylangelicin (XIX), crystallized from MeOH (0.18 g; m.p. 164°-5° C.). ##STR24##

Provenance & Evidence