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

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).

1. temperatureThe resulting mixture was heated
2. temperatureat reflux for 1 h
3. additionwas added
4. extractionIt was then extracted with diethyl ether
5. washThe extract was washed with saturated aqueous sodium bicarbonate
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by silica gel column chromatography
10. washeluting with an ethyl acetate

ORD record

ord-a8d6fd301b9042df9e581c2183911b1c

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07288541B2