HCID 13298918, compound → ANGELICIN,6-METHYL

HRID 359501Notes

Reaction equation

HRID 359501 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH2:13][CH:14]=C)[C:11]=1[OH:12])[O:8][C:7](=[O:16])[CH:6]=[CH:5]2>CCOC(C)=O>[CH3:1][C:2]1[CH:3]=[C:4]2[CH:5]=[CH:6][C:7]([O:8][C:9]2=[C:10]2[CH:13]=[CH:14][O:12][C:11]=12)=[O:16]

Participants

3

Reactant 1

HCID 13298918HCID 13298918, compound

Product 1

HCID 128912ANGELICIN,6-METHYL

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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.). ##STR25##

Workup

  1. temperaturecooled in an ice bath
  2. customa stream of ozonized oxigen was bubbled until 1.1 times the stoichiometric amount of ozone
  3. customThe catalyst was removed by filtration
  4. customthe solvent evaporated at reduced pressure
  5. additionthe residue treated with 85% H3PO4 (60 ml)
  6. temperaturechilled
  7. additiondiluted with H2O (200 ml)
  8. extractionextracted with CHCl3
  9. dry with materialFrom the dried (Na2SO4) organic phase the solvent
  10. customwas evaporated under reduced pressure
  11. customthe residue chromatographed on a silica gel column
  12. washby eluting with CHCl3

Sources & evidence

ORD record
ord-1d2b421d50694aacb6830a1f69f50f7d
Source dataset
uspto-grants-1991_03
Patent number
US05001147

Reaction notes

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