Methyl Acrylate → Methyl 3-(dimethoxyphosphinoyl)propionate

Participants

Reaction Conditions

Reaction Steps

This procedure was reported by; Kreutzkamp, N.; Mengel, W. Chem. Ber., 1967, 100, 709-714. ##STR8## A mixture of methyl acrylate (30 mL, 28.7 g, 0.33 mol) and dimethylphosphite (36.7 g, 0.33 mol) was cooled to 0° C. and treated with a solution of sodium methoxide (1M) in methanol (5 mL). After a few min a vigorous exothermic reaction took place. When the reaction subsided, an additional portion of sodium methoxide was added. This procedure was repeated for a total of four times. The reaction was then allowed to stir at room temperature for 16 h and then the methanol removed by distillation. The residue was then vacuum distilled, bp 95° C. @ 0.15mm, to provide 45.6 g, 70% of pure product. 1H NMR (CDCI3 /TMS/300 MHz) δ3.71(d, J=11.1 Hz, 6H), 3.67 (s, 3H), 2.57 (td, J=8.4, 12.5 Hz, 2H), 2.06(td, J=8.4 12.5 Hz, 2H); 31P NMR (CDCI3) 33.3 (s); 13C NMR (CDCI3) 172.3, 52.3(d, J=6.5 Hz), 51.8, 27.0(d, J=4.1 Hz), 20.8, 18.9.

Provenance & Evidence