Carbon Disulfide → 5-(3-Trimethoxysilylpropyloxymethyl)-1,3-oxathiolane-2-thione

Participants

Reaction Conditions

Reaction Steps

To a solution of (3-glycidoxypropyl)trimethoxy-silane (X=methoxy; 75.6 g, 320 mmol) and lithium bromide (1.38 g, 16.0 mmol) in tetrahydrofuran (250 ml), a solution of carbon disulfide (29.2 g, 384 mmol) in tetrahydrofuran (150 ml) was added dropwise at 0° C., and the mixture was stirred at 25° C. After 12 h, the volatiles were removed under reduced pressure, and the residue was dissolved in diethylether (500 ml), washed with saturated distilled water (200 ml) three times. The ether layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was distilled under vacuum to give 5-(3-trimethoxysilylpropyloxymethyl)-1,3-oxathiolane-2-thione (1a) as a yellow oil (51.2 g, 164 mmol, 51%).

Provenance & Evidence