Stannane, hydroxytrimethyl- → 3-[(2,6-Dimethylphenoxy)methylthio]propanoic acid

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Reaction Steps

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]+.

Provenance & Evidence