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(5S)-5-(((Tetrahydro-2H-Pyran-2-Yl)Oxy)Methyl)Dihydrofuran-2(3H)-One synthesis

3synthesis methods
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Yield:187264-97-7 93%

Reaction Conditions:

pyridinium 4-toluenesulfonate in dichloromethane at 20;

Steps:

52A

To a solution of (S)-5-(hydroxymethyl)dihydrofuran-2(3H)-one (1.0 g, 8.6 mmol, Acros) in dichloromethane (10 mL) were added 3,4-dihydro-2H-pyran (0.94 mL, 10.3 mmol, Aldrich) and pyridinium p-toluenesulfonate (0.22 g, 0.86 mmol, Aldrich). After stirring at room temperature overnight, the reaction mixture was washed with water (5 mL) and brine (5 mL). The organic extract was dried (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography using an Analogix Intelliflash280 (SiO2, 0-100% ethyl acetate in hexanes) to obtain 1.6 g (93%) of the title compound. MS (DCI/NH3) m/z 218 (M+NH4)+

References:

US2010/69348,2010,A1 Location in patent:Page/Page column 41