N,N,N',N'-tetraethylmethanediamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Malonic acid (5.2g) was added in portions to bis-diethylamino-methane (24g), cooled in ice and stirred manually. A violent reaction took place and the mixture became viscous. Evaportion of the excess bis-diethylamino-methane and diethylamine gave a syrup which was repeatedly recrystallised from acetone to give colourless crystals of 2-diethylaminomethylacrylic acid (5.9g, 76% melting point 121 to 3° C). cooled in ice A violent reaction

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-furfuryl alcohol (8.24 g; 84 mmol) in 55 ml of acetic acid was added dropwise a solution of N,N,N',N'-tetraethyl-methylenediamine (20 g; 126 mmol)in 25 ml of acetic acid, and the solution was stirred at 0° C. for 30 minutes and at room temperature for 17 hours. The above solution was concentrated in vacuo, the residue was basified with dropwise addition of 30% of NaOH solution at 0° C. (to pH=11), and the mixture was extracted with ethyl acetate. The mixture was filtered, the organic layer was dried over sodium sulfate and concentrated in vacuo to yield a brown oil. The oil was distilled with a Kugelrohr Apparatus to afford 12.33 g (80%) of 5-diethylaminomethyl-2-hydroxymethylfuran as a yellow oil, b.p. 140° C./1 mm. The above solution was concentrated in vacuo the residue was basified with dropwise addition of 30% of NaOH solution at 0° C. (to pH=11) the mixture was extracted with ethyl acetate The mixture was filtered the organic layer was dried over sodium sulfate concentrated in vacuo to yield a brown oil The oil was distilled with a Kugelrohr Apparatus

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Malonic acid (5.2g) was added in portions to bis-diethylamino-methane (24g), cooled in ice and stirred manually. A violent reaction took place and the mixture became viscous. Evaportion of the excess bis-diethylamino-methane and diethylamine gave a syrup which was repeatedly recrystallised from acetone to give colourless crystals of 2-diethylaminomethylacrylic acid (5.9g, 76% melting point 121 to 3° C). cooled in ice A violent reaction