Sodium hydride → isobutyl (E)-4-hydroxycrotonate

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Reaction Steps

To an ice cold solution of isobutyl 3,4-epoxybutanoate (300 g, 1.9 mol) in toluene (2.5 l), sodium hydride (55% suspension in oil, 3 g, 0.07 mol) was added portionwise. The solution was stirred at 0°-5° C. for 1 hour, then 55% sodium hydride (3 g, 0.07 mol) was added again. After stirring at room temperature for 1 hour the solution was washed with brine (0.4 1) containing 10% hydrochloric acid (60 ml), then twice with brine (300 ml each). The organic solution was dried over anhydrous sodium sulfate and evaporated to dryness. Distillation of the residue afforded 175 g (58.3%) of the title compound as a colourless oil, b.p. 89°-90° C. (0.5 mmHg). NMR (CDCl3): deltaH =7.05 (dt, J=15 and 4 Hz, 1H, CH=CH--CO), 6.12 (dt, J=15 and 2 Hz, 1H, CH=CH--CO), 4.40 (c.a, 2H, CH2OH). MS (E.I., 70 eV, 1.5 mA) m/z=127 (M--CH2OH)+, 85 (M--C3H5O2)+.

Provenance & Evidence