Sodium Carbonate → Diethyl 4-((hydroxyimino)(4-methoxyphenyl)methyl)benzylphosphonate

Participants

Reaction Steps

Diethyl 4-(4-methoxybenzoyl)benzylphosphonate, 32-d, (500 mg, 1.38 mmol) was dissolved in 95% EtOH (5 ml). Hydroxylamine hydrochloride (288 mg, 4.14 mmol) and Na2CO3 (439 mg, 4.14 mmol) was added to the solution. The reaction mixture was then stirred for 10 h under reflux. The resulting mixture was cooled to ambient temperature, filtered. The filtrate was concentrated under reduce pressure, extracted with ethyl acetate/H2O (3×10 ml). The organic layer was combined and washed with brine (2×10 ml) dried over Na2SO4 anhydrous, concentrated under reduce pressure to dry. The pure product, 32-e, was obtained as colorless oil (460 mg, 88% yield). 1H NMR (300 MHz, CDCl3) δ 0.67-0.85 (m, 6H), 2.628-3.306 (m, 2H), 3.30-3.35 (d, J=46.8, 3H), 3.51-3.63 (m, 4H), 6.31-6.33 (m, 1H), 6.44-6.47 (m, 1H), 6.74-6.92 (m, 6H). LC-MS 378 [MH]+.

Provenance & Evidence