Potassium Carbonate → HCID 178496529, Verbindung

Temperatur

50 °C

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).

1. customThe reaction mixture was quenched with water (10 mL)
2. extractionextracted with EtOAc (15 mL)
3. washThe organic layer was washed with water (10 mL)
4. washwashed with brine (10 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customto yield a yellow oil
9. customThe crude material was purified by silica gel chromatography on the combi-flash Rf system
10. additionThe fractions containing product
11. concentrationconcentrated under reduced pressure
12. customto yield a yellow oil, 0.140 g (45% yield)

ORD-Eintrag

ord-f66f1914d3ba4742b509ce62fead7cdd

Quelldatensatz

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09096624B2