Methanol → HCID 70294800, compound

To 150 mL methanol to which 4.2 mL 1.00N NaOH had been added was added 3-(7-methoxy-benzo[1,3]dioxol-5-yl)-5-hydroxy-5-(4-ethoxy-3-methylphenyl)-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one 2.00 g (3.95 mmol). The suspension was stirred to give solution and was placed in a 400 mL Pyrex™ beaker and diluted with 150 mL water. The beaker was covered with a quartz evaporating dish (100 mm o.d.×15 mm h., QRD 100; Quartz Scientific, Inc., Fairport Harbor, Ohio). The covered solution was irradiated for 20 hours in an Atlas Sunchex™ simulated sunlight exposure instrument (Xenon arc lamp, set to 0.35 W/m2 at 340 nm, filtered to exclude wavelengths less than 280 nm; Atlas Electric Devices Co., Chicago, Ill.). The mixture was filtered to remove insoluble solids, and the filtrate was evaporated in vacuo to remove 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 phase was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. Evaporation of the ether solution under reduced pressure gave a yellow solid, 340 mg. The residue was purified by chromatography on 50 g silica gel eluted with a gradient of 0% to 3% methanol in chloroform. The appropriate fractions were evaporated to a solid, 0.232 g. The product was identified by 1H NMR, MS, [M-H]+ =505.3 Da. and microanalysis.

1. customto give solution
2. customThe covered solution was irradiated for 20 hours in an Atlas Sunchex™
3. filtrationsunlight exposure instrument (Xenon arc lamp, set to 0.35 W/m2 at 340 nm, filtered to exclude wavelengths less than 280 nm; Atlas Electric Devices Co., Chicago, Ill.)
4. filtrationThe mixture was filtered
5. customto remove insoluble solids
6. customthe filtrate was evaporated in vacuo
7. customto remove methanol
8. extractionThe residual aqueous solution was extracted repeatedly with ethyl ether, while the pH of the aqueous phase
9. additionwas adjusted incrementally between 7.5 and 8 by addition of 3N HCl
10. extractionextracted with ethyl ether
11. washThe ether phase was washed with saturated sodium chloride solution
12. dry with materialdried over anhydrous magnesium sulfate
13. customEvaporation of the ether solution under reduced pressure
14. customgave a yellow solid, 340 mg
15. customThe residue was purified by chromatography on 50 g silica gel
16. washeluted with a gradient of 0% to 3% methanol in chloroform
17. customThe appropriate fractions were evaporated to a solid, 0.232 g

ORD record

ord-1a11f6ca98994fb59d23181f24021c3c

Source dataset

uspto-grants-2000_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06043241