Sodium borohydride → (E)-N,N-Diethyl-4-hydroxy-2-pentenamide

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Reaction Steps

To (E)-N,N-diethyl-4-oxo-2-pentenamide (0.73 g, 4.31 mmol) in methanol (10 ml) cooled to 0° C. is added sodium borohydride (0.18 g, 4.75 mmol) under nitrogen stirred for minutes, quenched with excess water, and extracted with ethyl acetate (3×50 ml). The organic extracts are combined, washed with saline (50 ml), dried over sodium sulfate, concentrated in vacuo to give the title compound, NMR (CDCl3) 6.89, 6.42, 4.49, 3.41, 2.51, 1.33, 1.17.

Provenance & Evidence