Ammonium Acetate → HCID 71239533, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(3-Methyl-butyryl)-benzoic acid ethyl ester (2000 mg, 8.536 mM), ammonium acetate (6580 mg, 85.4 mM) and sodium cyanoborohydride (1070 mg, 17.1 mmol) in methanol (17.1 mL) was heated to 60° C. for 6 h. The reaction was cooled, quenched with NH4Cl solution (10 mL). MeOH was removed under reduced pressure. The aqueous solution was extracted with EtOAc (3×30 mL). The organic solution was separated, dried (Na2SO4) and concentrated. The crude material was separated by a 40 g HC silica gel column with 0-15% MeOH in DCM. The desired product was collected as colorless oily material (1560 mg, 77.7%). 1H NMR (500 MHz, CDCl3) δ ppm 0.91 (dd, J=13.66, 6.59 Hz, 6 H) 1.40 (t, J=7.07 Hz, 3 H) 1.84-1.99 (m, 3 H) 4.27-4.42 (m, 3 H) 6.36 (br. s., 2 H) 7.51 (d, J=8.05 Hz, 2 H) 8.05 (d, J=8.05 Hz, 2 H). GC: m/z 235.

Provenance & Evidence