Carbon Disulfide → Ethyl acetate hexane

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Reaction Steps

Powdered potassium hydroxide (3.50 g, 62.50 mmole) is dissolved in 6.0 ml methanol and carbon disulfide (5.70 g, 75.0 mmole) is added at 0° C. The reaction mixture is shaken vigorously and 3,5-dimethoxy-4-methoxymethoxyphenyloxirane (29) (6.0 g, 25.0 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, and 2×30 ml ss NaCI. The ethyl acetate is reduced to 10 ml and 30 ml methanol along with 10 ml 5.0M methanolic HCl. The reaction is stirred for three hours, quenched with 100 ml H2O, extracted with ethyl acetate, 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 is recrystallized from hexane/ethyl acetate (4.52 g, 63% yield).

Provenance & Evidence