1,2-Dichloroethane → Ethyl 3-hydroxypentanoate

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Reaction Steps

The mixture of 1.9 g of ethyl R-(+)-3-butyryloxypentanate, 16 ml of 1,2-dichloroethane, 16 ml of ethanol and 0.3 ml of sulfuric acid was refluxed for 40 hours, water and ethyl acetate was added and the mixture was stirred. The separated organic layer was washed with a saturated aqueous solution of sodium bicarbonate and then with water, and dried on anhydrous magnesium sulfate. The solvent was distilled away, and 1.0 g crude product was obtained. The crude product was chromatographically purified, and 0.63 g of ethyl R-(-)-3-hydroxypentanate. [α]D24 =-29.7° (C=0.90, CHCl3). As described above, the optical purity of the obtained compound was tested by using Eu(hfc)3 as a shift agent. It was 88% ee. Moreover, the formulation of the above compounds was supported well by their NMR charts.

Provenance & Evidence