Sodium Bicarbonate → N-(1,4-dioxaspiro[4.5]dec-8-ylidene)-2-methylpropane-2-sulfinamide

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Reaction Steps

2-Methly-2-propanesulfinamide (7.4 g) is added to a solution of 1,4-dioxa-spiro[4.5]decan-8-one (10.0 g) and titanium tetraisopropoxide (37.9 mL) in tetrahydrofuran (130 mL) at room temperature. After stirring the solution at room temperature overnight, it is poured into a stirred saturated solution of NaHCO3 in water. The resulting mixture is filtered over Celite and the remainder in the filter is thoroughly washed with ethyl acetate. The organic phase of the filtrate is separated, washed with brine, and dried (MgSO4). The solvent is evaporated and the residue is chromatographed (cyclohexane/ethyl acetate 1:2→0:1) to give the title compound as a colorless solid. Yield: 7.0 g (42% of theory); TLC [silicagel, cyclohexane/ethyl acetate 1:2]: rf=0.5; Mass spectrum (ESI+): m/z=260 [M+H]+.

Provenance & Evidence