Potassium Bromide → tetrahydrofuro[2,3-b]furan-3(2H)-one

Temperature

-5 °C

Hexahydrofuro[2,3-b]furan-3-ol (55 g) was dissolved in dichloromethane (385 ml) sodium bicarbonate (10%, 165 ml) was added to it and cooled to −5° C. Potassium bromide (2.0 g), 2,2,6,6-Tetramethylpiperidin-1-yl)oxyl (TEMPO) (1.0 g) and Tetrabutyl ammonium bromide (1.0 g) was charged to the reaction. Sodium hypochlorite solution (365 ml) was added slowly by maintaining temp 0 to −6° C. Reaction mass was then maintained at 0 to −6° C. for 1 hr. Aqueous layer was separated and extracted with dichloromethane (2×110 ml) combined dichloromethane layers was washed with hydrochloride solution (10%, 110 ml) and Sodium thiosulphate solution (10%, 110 ml). Dichloromethane was then concentrated to residue, the residue was dissolved in isopropyl alcohol (40 ml) & methyl tert-butyl ether (40 ml) and cooled to 0-5° C., and filtered the solid to get the pure solid material of Tetrahydrofuro[2,3-b]furan-3(2H)-one (39 g) having purity 99.18%.

1. additionwas added to it
2. temperatureby maintaining temp 0 to −6° C
3. customReaction mass
4. temperaturewas then maintained at 0 to −6° C. for 1 hr
5. customAqueous layer was separated
6. extractionextracted with dichloromethane (2×110 ml)
7. washwas washed with hydrochloride solution (10%, 110 ml) and Sodium thiosulphate solution (10%, 110 ml)
8. concentrationDichloromethane was then concentrated to residue
9. dissolutionthe residue was dissolved in isopropyl alcohol (40 ml)
10. temperaturemethyl tert-butyl ether (40 ml) and cooled to 0-5° C.
11. filtrationfiltered the solid

ORD record

ord-64a1345493194e608da2a808afeeaad0

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841467B2