Methanol → HCID 44214242, compound

To 150 mL methanol to which 3.95 mL 1.00N NaOH had been added was added 3-benzo[1,3]dioxol-5-yl-5-hydroxy-5-(4-methoxyphenyl)-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 30 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. Addition of petroleum ether gave a crystalline solid which was filtered and dried under vacuum at 40° C., giving a solid melting at 192-193° C., 180 mg. 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 30 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. additionAddition of petroleum ether
14. customgave a crystalline solid which
15. filtrationwas filtered
16. customdried under vacuum at 40° C.

ORD record

ord-e668846ec82342609a08576e77784edb

Source dataset

uspto-grants-2000_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06043241