Potassium Hydroxide → 6,5'-Dimethylangelicin

HRID 359500Notes

Reaction equation

HRID 359500 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH2:16][CH:17](Br)[CH2:18]Br)[C:11]=1[O:12]C(=O)C)[O:8][C:7](=[O:21])[CH:6]=[CH:5]2.[OH-].[K+].O1C2C(=CC=CC=2)C=CC1=O.[OH-].[K+]>O>[CH3:18][C:17]1[O:12][C:11]2[C:10](=[C:9]3[O:8][C:7](=[O:21])[CH:6]=[CH:5][C:4]3=[CH:3][C:2]=2[CH3:1])[CH:16]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 13298924HCID 13298924, compoundHCID 131716810HCID 131716810, compound

Product 1

HCID 1461586,5'-Dimethylangelicin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ethanolic solution (100 ml) of 6-methyl-7-acetoxy-8-(2',3'-dibromopropyl) coumarin (XIII) (1.5 g) a volume of ethanolic 4% KOH solution was added, equivalent to a molar ratio coumarin/KOH 1:10. The mixture was refluxed for 80 min. in the dark, chilled, diluted with H2O (200 ml) and acidified with dil. HC1. The precipitate thus obtained was filtered, washed with H2O, dried and chromatographed on a silica gel column by eluting with CHC13, yielding the 6,5'-dimethylangelicin (XVI), crystallized from MeOH (0.52 g; m.p. 175-6° C.). ##STR22##

Workup

  1. temperatureThe mixture was refluxed for 80 min. in the dark,
  2. temperaturechilled
  3. customThe precipitate thus obtained
  4. filtrationwas filtered
  5. washwashed with H2O
  6. customdried
  7. customchromatographed on a silica gel column
  8. washby eluting with CHC13

Sources & evidence

ORD record
ord-b813226fd0e74aab9f4c96b078454672
Source dataset
uspto-grants-1991_03
Patent number
US05001147

Reaction notes

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