Allyl bromide → HCID 10630623, compound

Participants

Reaction Steps

Ethyl hydroxyacetate was added dropwise to a slurry of NaH (1.1 eq) in DMF at 0° C. and the resulting mixture was stirred at RT for 2 h. After cooling to 0° C., allylbromide (1.1 eq) was added dropwise via syringe and the reaction mixture was stirred at RT for 2 h, quenched by careful addition of sat. aq. NH4Cl and partitioned between Et2O and brine. The organic layer was dried (Na2SO4) and concentrated under reduced pressure to give the title compound as pale yellow oil. 1H NMR (300 MHz, CDCl3) δ 5.91 (m, 1H), 5.30 (dd, J 17.2, 1.5, 1H), 5.24 (dd, J 10.6, 0.6, 1H), 4.23 (q, J 2.1, 2H), 4.10 (d, J 5.7, 2H), 4.08 (s, 2H), 1.29 (t, J 7.08, 3H).

Provenance & Evidence