Carbon Tetrachloride → (2R, 3S)-(-)-3-[8-(methoxyethoxymethoxy)octyl]oxirane-2-carboxylic acid

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Reaction Steps

2.5 ml of tetrachloromethane, 2.5 ml of acetonitrile, 3.9 ml of water, 1.5 mmol of the alcohol 5, 4.5 mmol of sodium periodate and 5 mol % of ruthenium(III) chloride trihydrate are combined in this sequence, and the mixture is stirred overnight at room temperature. The batch is evaporated, and the residue is taken up in 10 ml of saturated NaCl solution and 8 ml of CH2Cl2. The phases are separated, the aqueous phase is extracted with CH2Cl2, the combined organic phases are washed with saturated NaCl solution and dried over MgSO4, and the solvent is removed in vacuo. The oxiranecarboxylic acid obtained is employed without further purification.

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