反应详情

To a solution of (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(phenoxymethyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (5.5 g, 9.54 mmol), in acetic acid (23.62 mL) under nitrogen atmosphere, was added 37% HBr/AcOH (47.7 mL). The reaction mixture was stirred at r.t. for 3 h. After the completion of the reaction as confirmed by TLC, the reaction mixture was cooled to 0° C. and quenched very slowly with saturated solution of potassium carbonate until effervescence ceases. The crude compound was extracted with ethyl acetate (2×300 mL). The organic layer was separated, dried over Na2SO4 and concentrated in vacuo to afford crude compound which was purified by column chromatography (silica gel, 3:7 Ethyl acetate:Pet ether) to afford the title compound (4.28 g, 79%) as a white solid.

1. customAfter the completion of the reaction
2. temperaturethe reaction mixture was cooled to 0° C.
3. customquenched very slowly with saturated solution of potassium carbonate until effervescence ceases
4. extractionThe crude compound was extracted with ethyl acetate (2×300 mL)
5. customThe organic layer was separated
6. dry with materialdried over Na2SO4
7. concentrationconcentrated in vacuo
8. customto afford crude compound which
9. customwas purified by column chromatography (silica gel, 3:7 Ethyl acetate:Pet ether)