反应详情

A 50-mL flask equipped with reflux condenser and a magnetic stirring bar was charged with 0.254 g (1 mmol) of methyl 3-[(2,6-dimethylphenoxy)methylthio]propanoate and 0.362 g (2 mmol) of trimethyltin hydroxide dissolved in 25 mL of 1,2-dichloroethane and was refluxed overnight under an argon atmosphere. The solvent was removed under reduced pressure, the organic residue was dissolved in 40 mL of ethyl acetate, extracted 3 times with 10 mL 5% HCl, then with 10 mL brine, and dried with anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the reddish residue was purified by normal-phase (COMBIFLASH) chromatography with a hexane/ethyl acetate (95:5, 7 minutes; 95:40, 15 minutes) to afford 0.2 g (83%) of 3-[(2,6-dimethylphenoxy)methylthio]propanoic acid 29. 1H NMR (400 MHz, CDCl3): 2.33 (s, 6H), 2.78-2.82 (t, 2H, J=7.2 Hz), 3.03-3.07 (t, 2H, J=7.2H), 4.99 (s, 2H), 6.94-7.04 (m, 3H), 10.98 (b, OH). MS (ESI): 241 [M+H]+; 263 [M+Na]+.

1. customA 50-mL flask equipped
2. temperaturewith reflux condenser and a magnetic stirring bar
3. temperaturewas refluxed overnight under an argon atmosphere
4. customThe solvent was removed under reduced pressure
5. dissolutionthe organic residue was dissolved in 40 mL of ethyl acetate
6. extractionextracted 3 times with 10 mL 5% HCl
7. dry with materialwith 10 mL brine, and dried with anhydrous magnesium sulfate
8. customThe solvent was removed under reduced pressure
9. customthe reddish residue was purified by normal-phase (COMBIFLASH) chromatography with a hexane/ethyl acetate (95:5, 7 minutes; 95:40, 15 minutes)