反应详情

To a solution of 0.112 g (2.81 mmol) of 60% sodium hydride in 2 mL of THF, cooled to 0° C., was added a solution of 0.500 g (2.81 mmol) of 4-but-2-ynyloxy-benzenethiol, dissolved in 3 mL of THF. The resulting mixture was stirred for 0.5 h at room temperature, then cooled to 5° C., followed by the addition of 0.518 g (3.65 on mol) of neat 2,7-dioxaspiro[3,5]nonane-1-one while keeping the reaction temperature below 10° C. The reaction was allowed to warm to room temperature and stirred for an additional 0.5 h and then quenched with 3 mL of 3N HCl solution and 3 mL of water. The resulting mixture was extracted with dichloromethane and the combined organics were washed with water and brine, dried over Na2SO4, filtered through a plug of silica gel and concentrated in vacuo. The residue was triturated with hexanes and acetonitrile and filtered to give 0.72 g of the carboxylic acid as a semi-solid. Electrospray Mass Spec: 319 (M−H)−

1. temperaturecooled to 5° C.
2. customthe reaction temperature below 10° C
3. temperatureto warm to room temperature
4. stirringstirred for an additional 0.5 h
5. customquenched with 3 mL of 3N HCl solution and 3 mL of water
6. extractionThe resulting mixture was extracted with dichloromethane
7. washthe combined organics were washed with water and brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered through a plug of silica gel
10. concentrationconcentrated in vacuo
11. customThe residue was triturated with hexanes and acetonitrile
12. filtrationfiltered