4-Iodomethyl-tetrahydro-pyran-4-carboxylic acid methyl ester → Methyl 4-[(acetylsulfanyl)methyl]oxane-4-carboxylate

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Reaction Steps

4-Iodomethyl-tetrahydro-pyran-4-carboxylic-acid methyl ester (305 g) was dissolved in N,N-dimethylformamide (20 ml) at room temperature and potassium thioacetate (1.47 g) added. The mixture was stirred for 18 hours then diluted with water (50 ml) and extracted with diethyl ether (4×25 ml). The combined organics were washed with saturated sodium bicarbonate solution (3×20 ml) and brine (20 ml), then dried (MgSO4), filtered and evaporated under reduced pressure to give the title compound as a yellow solid (2.42 g, 97%).

Provenance & Evidence