Allyl Alcohol → HCID 18441987, compound

Participants

Reaction Steps

To a CH2Cl2 (40 mL) solution of 2,4-difluorophenyl acetic acid (6.89 g, 40.03 mmol) at 0° C. was added DMAP (4.89 g, 40.03 mmol), and Meldrum's Acid (5.77 g, 40.03 mmol) followed by DCC (8.26 g, 40.03 mmol). The reaction mixture was warmed to ambient temperature and stirred for 4 h. The reaction was filtered to remove the DCU and the filtrate washed with 1N HCl, H2O, and brine. The organics were dried (Na2SO4), filtered and concentrated to a yellow oil. The residue was redissolved in THF (40 mL) and allyl alcohol (8 mL, 117.63 mmol). The reaction mixture was refluxed for 3 h and then concentrated to deliver 9.67 g (95% yield) of the title compound as a pale yellow oil and used without further purification. 1H NMR (CDCl3, 400 MHz) δ 7.16–7.10 (m, 1H), 6.82 (dd, J=16.6, 8.2 Hz, 2H), 5.91–5.82 (m, 1H), 5.31 (dd, J=17.3, 1.4 Hz, 1H), 5.25 (dd, J=10.3, 1.0 Hz, 1H), 4.61 (d, J=5.8 Hz, 2H), 3.82 (s, 2H), 3.52 (s, 2H).

Provenance & Evidence