Water → HCID 178527067, compound

Participants

Reaction Conditions

Reaction Steps

1.1 g (0.0275 mol) sodium hydride (60% content) is added to a 100 ml three-necked bottle under the protection of nitrogen, paraffin oil is removed by rinsing twice with 10 ml n-hexane each time; then, 10 ml methylbenzene is added, 8.6 g tetraethyl methylenediphosphonate (0.03 mol) is dropwise added to the solution of 20 ml methylbenzene under magnetic stirring, the temperature of cold water bath is maintained within a range from 10 to 15° C. while addition, a large amount of gas is discharged, the addition can be finished about half an hour later, and stirring is continued for reaction for half an hour; afterwards, 5.1 g C-14 aldehyde (3B) (prepared in the embodiment 3, 0.025 mol) is dropwise added and dissolved in the solution of 20 ml methylbenzene, the temperature of cold water bath is maintained within a range from 10 to 15° C. while addition, the addition can be finished about half an hour later, and stirring is continued for reaction for half an hour. 20 ml water is added to the reaction mixture solution, which is followed by stirring for 10 minutes and layering, organic layer is rinsed by 20 ml sodium hydride aqueous solution with the concentration of 10%, dried by magnesium sulfate and filtered, and the solvent is dried by evaporation under reduced pressure to obtain 7.3 g 1,3,6,10-tetra-double bond pentadec-carbon phosphonate (4) crude product, which is light brown liquid and has the gas phase content of 93.5% and the yield of 86.1%. The product's NMR spectroscopy is consistent with the embodiment 4.

Provenance & Evidence