Reacción #57038

Ecuación de reacción

Diethyl aminomethylphosphonate

2-furan boronic acid

glyoxylic acid monohydrate

NH4OH

→

clear oil

Rendimiento 67.0%

2-((Diethoxvphosphoryl)methylamino)-2-(furan-2-yl)acetic acid

Rendimiento 67.0%

Disolventes

dichloromethane

ethyl acetate

MeOH

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas put into a 10ml round bottom flask
2. 2
   OtroSolvent was then removed
3. 3
   Otroproduct was isolated by flash column chromatography

Procedimiento

Diethyl aminomethylphosphonate, prepared according to literature (Davidsen, S. K.; Philips, G. W.; Martin, S. F. Organic Synthesis CV 8, 451.) (50 mg, 0.3 mmol), 2-furan boronic acid (67 mg, 0.6 mmol), glyoxylic acid monohydrate (28 mg, 0.3 mmol) was put into a 10ml round bottom flask, dissolved with 5 ml of acetonitrile. The mixture was stirred at room temperature for one day. Solvent was then removed and product was isolated by flash column chromatography using NH4OH 5%, MeOH 20%, ethyl acetate 55%, dichloromethane 20% afforded 60 mg clear oil (67% yield). 1H NMR (360 MHz, CDCl3) δ 1.23-1.33(td, J=7.3, 1.7 Hz, 6H), 2.86-2.98(d, J=13.3 Hz, 2H), 4.02-4.14(m, 4H), 4.49(s, 1H), 6.26-6.31(dd, J=3.2, 1.8 Hz, 1H), 6.31-6.36(d, J=3.2 Hz, 1H), 7.33-7.38(bs, 1H); 13C NMR (126 MHz, CDCl3) δ 16.30(d, J=6 Hz), 41.51(d, J=156.5 Hz), 60.81(d, J=14.7 Hz), 62.40(t, J=6.8 Hz), 108.97, 110.27, 142.41, 151.19, 173.29.

Fuente