Hydrochloric Acid → Methyl 3-oxoheptanoate

Participants

Reaction Steps

After stirring for 20 minutes, 9.3 ml of methyl acetoacetate were dropped, stirring was continued for 30 minutes at 0° C. and further 54 ml of butyllithium 1.6M in hexane were dropped. After further 30 minutes 8.4 ml of propyl iodide were dropped into the dark orange solution. The temperature was allowed to raise to room temperature and after 30 minutes, 50 ml of 37% HCl diluted with 100 ml of H2O were continuously dropped while keeping the temperature under 15° C. The reaction mixture was extracted with Et2O. The organic phase was washed with a NaCl saturated solution, dried on Na2SO4 and evaporated to dryness. The residue was purified by FC (eluent: AcOEt/hexane 1:9). 8.3 g of a clear oil were obtained (yield 61%); 1H-NMR (200 MHz, CDCl3)δ: 0.90 (t, 3H), 1.22-1.65 (m, 4H), 2.53 (t, 2H), 3.44 (s, 2H), 3.73 (s, 3H).

Provenance & Evidence