Hydrochloric Acid → HCID 67513093, compound

Participants

Reaction Steps

To a 0° C. solution of 3-[4-(2-chloroethoxy)-3-iodophenyl]propan-1-ol (Step B) (1.00 g, 2.94 mmol) in THF (10 ml) was added potassium tert-butoxide (1M in THF) (6.61 ml, 6.61 mmol). The resulting solution was warmed to RT (turned cloudy) and stirred under nitrogen for 3 hours. Dilute HCl was added to the mixture and extracted 2 times with ethyl acetate. The combined organics were washed with brine and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc in hexanes to afford the title compound. 1H NMR (500 MHz, CD3OD): δ 7.66 (s, 1H); 7.23-7.13 (m, 1H); 6.96-6.88 (m, 1H); 6.66 (ddd, J=28.0, 13.7, 6.2 Hz, 1H); 4.64-4.60 (m, 1H); 4.43 (dd, J=6.1, 1.6 Hz, 1H); 3.54 (t, J=6.4 2H); 2.62 (t, J=7.6 Hz, 3H); 1.81-1.74 (m, 3H).

Provenance & Evidence