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

Participants

Reaction Conditions

Reaction Steps

In a 250 mL round bottom flask, NaOCl (6.15 g, 14% w/w) was diluted in 100 mL of water. The pH of the solution was adjusted to 9.5 using a 1M NaHCO3 aqueous solution. In a separate 250 mL round bottom flask, hexahydrofuro[2,3-b]furan-3-ol (1 g, 7.7 mmol, 1 eq.) was dissolved in 15 mL of AcOEt at 0° C. Then KBr (91 mg, 0.77 mmol, 0.1 eq.) dissolved in 1 mL of water was added followed by the addition of TEMPO (12 mg, 0.08 mmol, 0.01 eq.). Finally, the NaOCl mixture was added dropwise. After 15 minutes of stirring at 0° C., the mixture was extracted 3 times with 100 mL of AcOEt. The collected organic layers were dried over Na2SO4 and the solvent was evaporated under reduced pressure to afford 950 mg of a white solid, yield: 96%. The resulting tetrahydrofuro[2,3-b]furan-3(2H)-one was used in the next step without further purification.

Provenance & Evidence