反应详情

To a 3-L three-neck round-bottom flask equipped with an overhead mechanical stirrer, addition funnel and a N2 inlet was added ethyl 2-[4-(chlorosulfonyl)phenoxy]-2-methylpropanoate (53 g, 0.173 moles, 1 eq) and absolute EtOH (500 ml). Tin powder (325 mesh, 123.06 g, 1.04 moles, 6 eq) was added as a solid. The overhead stirrer was adjusted so that the rotor is as close as possible to the bottom of the round-bottom flask and stirring speed was accelerated to a very high setting before adding the HCl to prevent the clumping of the tin metal. Hydrogen chloride (4N in dioxane, 300 ml) was added dropwise over the course of 1 hour. The reaction mixture was refluxed for 4 hours at which point the hot ethanolic solution was poured into a 2-L Erlenmeyer flask containing CH2Cl2 (1 L) and ice. After stirring for 10 minutes the biphasic mixture was filtered through Celite. After transferring to a separatory funnel the phases were separated and the aqueous fraction was washed with CH2Cl2 (2×100 ml). The combined organic fractions were dried over Na2SO4, filtered and concentrated in vacuo. A bright yellow oil with a white precipitate suspended resulted. This yellow mixture was dissolved in a minimum amount of CH2Cl2 and filtered once again through Celite to yield 30 g (75%) of a bright yellow oil.

1. customTo a 3-L three-neck round-bottom flask equipped with an overhead mechanical stirrer, addition funnel and a N2 inlet
2. customas close as possible to the bottom of the round-bottom flask
3. temperatureThe reaction mixture was refluxed for 4 hours at which point the hot ethanolic solution
4. additionwas poured into a 2-L Erlenmeyer flask
5. stirringAfter stirring for 10 minutes the biphasic mixture
6. filtrationwas filtered through Celite
7. customAfter transferring to a separatory funnel
8. customthe phases were separated
9. washthe aqueous fraction was washed with CH2Cl2 (2×100 ml)
10. dry with materialThe combined organic fractions were dried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. customA bright yellow oil with a white precipitate suspended resulted
14. filtrationfiltered once again through Celite