Acetic Acid → 1-Chloro-3-[(prop-2-en-1-yl)oxy]propan-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of iPr2Net (3.1 eq) in THF at −78° C. was added dropwise BuLi (1.4 M. in hexanes, 3.1 eq). The resulting mixture was stirred at 0° C. for 15 min, cooled again to −78° C. and added via cannula to a solution of ethyl (allyloxy)acetate from Step 1(1 eq) and iodochloromethane (2.5 eq) in Et2O at −78° C. After stirring 30 min at −78° C., a solution of AcOH (25 eq.) in THF was added dropwise and the resulting mixture was stirred at RT for 15 min and partitioned between Et2O and brine. The organic layer was washed with sat. aq. NaHCO3, brine, dried (Na2SO4) and concentrated under reduced pressure. The crude residue was purified by SiO2 gel chromatography (hexane/Et2O=9/1) to give the title compound as a colourless oil. 1H NMR (300 MHz, CDCl3) δ 5.90 (m, 1H), 5.35-5.25 (m, 2H), 4.30 (s, 2H), 4.24 (s, 2H), 4.07 (d, J 5.5, 2H).

Provenance & Evidence