Potassium Carbonate → HCID 178496529, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (3-methoxy-4-nitrobenzyl)methylphosphinic acid (Compound 216C, 0.250 g, 1.02 mmol) and 1-bromo-2-methoxy ethane (0.287 mL, 3.06 mmol) in DMF (3.0 mL) was charged with potassium carbonate (0.169 g, 1.22 mmol) and n-Bu4NI (0.188 g, 0.510 mmol). The reaction mixture was allowed to heat at 50° C. for 16 hours with stirring. The reaction mixture was quenched with water (10 mL) and extracted with EtOAc (15 mL). The organic layer was washed with water (10 mL), washed with brine (10 mL), dried over Na2SO4, filtered, concentrated under reduced pressure to yield a yellow oil. The crude material was purified by silica gel chromatography on the combi-flash Rf system using 1:1 EtOAc-DCM/MeOH (100:0→90:10) as eluent. The fractions containing product were combined and concentrated under reduced pressure to yield a yellow oil, 0.140 g (45% yield). 1H NMR (CDCl3, 400 MHz): δ=1.47 (d, J=13.89 Hz, 3 H), 3.24 (dd, J=17.43, 3.79 Hz, 2 H), 3.39 (s, 3 H), 3.51-3.62 (m, 2 H), 3.98 (s, 3 H), 4.14 (ddd, J=8.27, 4.42, 4.23 Hz, 2 H), 6.93 (dt, J=8.34, 1.89 Hz, 1 H), 7.12 (t, J=1.77 Hz, 1 H), 7.85 (dd, J=8.21, 0.63 Hz, 1 H). MS (ES+): m/z 304.08 [MH+] (TOF, polar).

Provenance & Evidence