Carbon Disulfide → Ethyl acetate hexane

Participants

Reaction Steps

Powdered potassium hydroxide (1.75 g, 31.25 mmole) is dissolved in 3.0 ml methanol and carbon disulfide (2.85 g, 37.5 mmole) was added at 0° C. The reaction mixture is shaken vigorously and 3,5-dimethoxy-4-methoxymethoxyphenyloxirane (29) (3.0 g, 12.5 mmole) is added. The reaction is allowed to warm to room temperature at which point the reaction starts to reflux. The reaction is stirred at room temperature for 24 hours, and is quenched with ethyl acetate and 10% NaOH. The organic layer is washed with 3×40 ml 10% NaOH, 1×30 ml H2O, 2×30 ml ss NaCl, dried over MgSO4, and evaporated in vacuo to a yellow oil which is purified by flash column chromatography using 2:1 hexane/ethyl acetate. The product was recrystallized from hexane/ethyl acetate (4.52 g, 63% yield).

Provenance & Evidence