Toluene → HCID 15878269, compound

Participants

Reaction Steps

To 118 mg (1 mmol) of α-methylstyrene and 130 mg (1 mmol) of n-butylglyoxylate was added at 0° C. the solution of the complex in toluene obtained in Example 1 (2). After stirring for 1 hour, the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate and filtered through celite. Then the filtrate was extracted with ether thrice and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1). Thus 213 mg of n-butyl 2-hydroxy-4-phenyl-4-pentenoate was obtained (yield: 82%). When measured with CHIRALPAK AS column (manufactured by Daicel Chemical Industries) [hexane:i-PrOH=3:1, flow rate: 0.5 ml/min], the optical purity of this product was 97.5% e.e.

Provenance & Evidence