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

Temperature

0 °C

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).

1. temperaturecooled again to −78° C.
2. stirringAfter stirring 30 min at −78° C.
3. stirringthe resulting mixture was stirred at RT for 15 min
4. custompartitioned between Et2O and brine
5. washThe organic layer was washed with sat. aq. NaHCO3, brine
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated under reduced pressure
8. customThe crude residue was purified by SiO2 gel chromatography (hexane/Et2O=9/1)

ORD record

ord-ca0e6a263ae74d98ad1c4355f41aeed7

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08178520B2