Acetonitrile → (4S)-4-tert-butyl-1,3,2-dioxathiolane 2,2-dioxide

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Reaction Steps

To 5.63 g (47.63 mmol) of (2S)-3,3-dimethyl-1,2-butanediol in 48 mL of carbon tetrachloride was added 3.47 mL (47.63 mmol) of thionyl chloride. The resulting mixture was heated at reflux for 1 h, and cooled to 0° C., before 48 mL of acetonitrile was added. Then, 1.0 mg (4.8 μmol) of ruthenium(III) chloride hydrate was added, followed by 15.28 g (71.45 mmol) of sodium periodate. The reaction mixture was diluted with 71 mL of water and stirred for 2 h. It was then extracted with diethyl ether. The extract was washed with saturated aqueous sodium bicarbonate, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel column chromatography eluting with an ethyl acetate:hexanes solution (3:7) to give 8.33 g (97%) of (4S)-4-tert-butyl-1,3,2-dioxathiolane 2,2-dioxide. Rf=0.30 (3:7 ethyl acetate:hexanes); 1H-NMR (300 MHz, DMSO-d6): δ 4.99–4.88 (m, 2H), 4.78 (t, J=8 Hz, 1H), 0.94 (s, 9H).

Provenance & Evidence