反应详情

温度

0 °C

A solution composed of 10 g (70 mmol) of 3-methyl-2-thiophenecarboxylic acid, 3.4 g (56 mmol) of nitromethane and 115 ml of DMF is cooled to 0° C. 11.9 g (72.8 mmol) of diethyl cyanophosphonate in 56 ml of DMF, and then 18.2 g (180 mmol) of triethylamine in 56 ml of DMF are added thereto successively. The medium is then stirred for 2 hours at 0° C. and for 21 hours at room temperature. The reaction medium is poured over 1 litre of a toluene/ethyl acetate (1:1) mixture, and extracted with water. This aqueous phase, acidified with 40 ml of acetic acid, is extracted with a toluene/ethyl acetate (1:1) mixture. The organic extracts are washed with water and then with a saturated NaCl solution in water, before being dried over Na2SO4 and concentrated. The residue, purified by chromatography on a silica column in dichloromethane and then by recrystallization from an ethyl acetate-hexane mixture, gives 2 g of a pale yellow solid (Yield=19%)

1. extractionextracted with water
2. extractionis extracted with a toluene/ethyl acetate (1:1) mixture
3. washThe organic extracts are washed with water
4. dry with materialwith a saturated NaCl solution in water, before being dried over Na2SO4
5. concentrationconcentrated
6. customThe residue, purified by chromatography on a silica column in dichloromethane
7. customby recrystallization from an ethyl acetate-hexane mixture