Methanol → HCID 9957850, compound

HRID 1637582Notes

Reaction equation

HRID 1637582 reaction equation
CO.[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][C:13]3[C:17]([OH:30])([C:18]4[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=4)[O:16][C:15](=[O:31])[C:14]=3[C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)=[CH:11][C:6]=2[O:5][CH2:4]1>O>[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12]/[C:13](/[C:17](=[O:30])[C:18]3[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=3)=[C:14](/[C:32]3[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=3)\[C:15]([OH:31])=[O:16])=[CH:11][C:6]=2[O:5][CH2:4]1

Participants

4

Reactant 2

HCID 887MethanolHCID 15453533HCID 15453533, compound

Product 1

HCID 9957850HCID 9957850, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 250 mL methanol was added 4-benzo[1,3]dioxol-5-ylmethyl-5-hydroxy-3-(4-methoxy-phenyl)-5-(3,4,5-trimethoxy-phenyl)-5H-furan-2-one 4.0 g (7.89 mmol), giving solution. To the solution was added 250 mL water containing 15.8 mL 1.001N NaOH. The solution was irradiated with a Hanovia ultraviolet light contained in a quartz reactor (Ace Glass, Catalog 1200, #7840-180) for 16 hours at ambient temperature. The solution was evaporated in vacuo to remove the methanol. The residual aqueous solution was extracted repeatedly with ethyl ether, while the pH of the aqueous phase was adjusted incrementally between 7.5 and 8 by addition of 3N HCl. The aqueous phase was then acidified to pH 1 with HCl and extracted with ethyl ether. The ether extract was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. Evaporation of the ether solution under reduced pressure gave a foam, 1.44 g. The residue was purified by chromatography on 50 g silica gel eluted with 1% methanol in chloroform. The appropriate fractions were evaporated to a solid, 0.77 g. The product was identified by 1H NMR, MS [M-H]+ =505.4 Da. and microanalysis.

Workup

  1. customgiving solution
  2. customThe solution was irradiated with a Hanovia ultraviolet light
  3. customcontained in a quartz reactor
  4. customThe solution was evaporated in vacuo
  5. customto remove the methanol
  6. extractionThe residual aqueous solution was extracted repeatedly with ethyl ether, while the pH of the aqueous phase
  7. additionwas adjusted incrementally between 7.5 and 8 by addition of 3N HCl
  8. extractionextracted with ethyl ether
  9. extractionThe ether extract
  10. washwas washed with saturated sodium chloride solution
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customEvaporation of the ether solution under reduced pressure
  13. customgave a foam, 1.44 g
  14. customThe residue was purified by chromatography on 50 g silica gel
  15. washeluted with 1% methanol in chloroform
  16. customThe appropriate fractions were evaporated to a solid, 0.77 g

Sources & evidence

ORD record
ord-4fe7b617d0554585a47a9b44ebc1c63b
Source dataset
uspto-grants-2000_03
Patent number
US06043241

Reaction notes

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