methyl 3-ethylpent-2-enoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-ethyl pent-2-enoic acid methyl ester (200 mg, 1.4 mmol) was dissolved in dioxane (1 ml). 1N NaOH (1 ml) was added, and the mixture was left overnight at 50° C.; 1N hydrochloric acid was added (2 ml), and the compound was extracted with ethyl acetate. The organic solution was dried over sodium sulfate, filtered and the solvent was removed under reduced pressure, obtaining 162 mg of 3-ethylpent-2-enoic acid as colourless oil. Yield 90%. 1H-NMR: (CDCl3, 500 MHz) chemical shift p.p.m. 1.06–1.11 (m, 6H, CH2CH3); 2.23 (q, 2H, CH3CH2); 2.64 (q, 2H, CH3CH2); 5.65 (s, 1H, CHC(O)). the compound was extracted with ethyl acetate The organic solution was dried over sodium sulfate filtered the solvent was removed under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-ethyl-pent-2-enoic acid methyl ester (150 mg, 1.056 mmol) was dissolved in dioxane (1 ml), and palladium 10% on activated carbon (30 mg) was added; the slurry was hydrogenated under pressure (40 p.s.i.) for 4 h. The carbon was filtered off and the filter was washed with dioxane (1 ml); 1N NaOH (2 ml) was added to the mixture which was left overnight at room temperature; after addition of 1N hydrochloric acid (3 ml), the product was extracted with ethyl acetate. The organic solution was dried over sodium sulfate, filtered and the solvent was removed under reduced pressure, obtaining 90 mg of 3-ethyl pentanoic acid as colourless oil. Yield 65.5%. The carbon was filtered off the filter was washed with dioxane (1 ml) 1N NaOH (2 ml) was added to the mixture which was left overnight at room temperature after addition of 1N hydrochloric acid (3 ml) the product was extracted with ethyl acetate The organic solution was dried over sodium sulfate filtered the solvent was removed under reduced pressure