Potassium Bromide → HCID 12895803, compound

Participants

Reaction Steps

To a solution of (1S,5R,6R,7R)-3-oxo-6-hydroxymethyl-7-(2-tetrahydropyranyloxy)-2-oxabicyclo[3.3.0]octane (140.5 g; J. Am. Chem. Soc., 98, 1490 (1971)) in ethyl acetate (4100 ml), water (410 ml), sodium acetate (134.9 g), potassium bromide (6.53 g) and 2,2,6,6-tetramethyl-1-piperidinyloxyradical (TEMPO; 2.14 g) were added. The mixture was cooled with sodium chloride-water. The reaction mixture was stirred vigorously. Thereto, a solution of 10% sodium hypochlorous acid (302 ml) which was saturated with sodium hydrogencarbonate was added at a dropwise for 40 minutes. After reaction, the organic layer was washed by an aqueous saturated solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the title compound (113.6 g).

Provenance & Evidence