Sodium hydride → isobutyl (E)-4-hydroxycrotonate

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)+.

1. stirringAfter stirring at room temperature for 1 hour the solution
2. washwas washed with brine (0.4 1)
3. additioncontaining 10% hydrochloric acid (60 ml)
4. dry with materialThe organic solution was dried over anhydrous sodium sulfate
5. customevaporated to dryness
6. distillationDistillation of the residue

ORD record

ord-9dfccceb37b0422caf7bd060dcab66b0

Source dataset

uspto-grants-1992_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05130319