4-Nitrobenzaldehyde → Diethyl [2-(4-nitrophenyl)ethenyl]phosphonate

Reaction equation

CC[O-].[Na+].[N+:5]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1)([O-:7])=[O:6].[CH2:16](P(=O)(OCC)OCC)[P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20]>CO>[CH2:19]([O:18][P:17]([CH:16]=[CH:12][C:11]1[CH:14]=[CH:15][C:8]([N+:5]([O-:7])=[O:6])=[CH:9][CH:10]=1)(=[O:24])[O:21][CH2:22][CH3:23])[CH3:20]

Participants

Procedure

Sodium ethylate (4.95 g, 72.8 mmol) is added to a solution of 4-nitrobenzaldehyde (10 g, 66.2 mmol) in 200 ml of methanol, and tetraethyl methylenediphosphonate (21 g, 72.8 mmol) is then added dropwise. After 2 h of stirring at room temperature, a further 0.43 g of sodium ethylate and 2 g of tetraethyl methylene diphosphonate are added. After 15 min of stirring at room temperature, the ethanol is evaporated off under vacuum and the residue is bipartitioned in a water/ethyl acetate mixture. The organic phase is washed with water, then dried (MgSO4) and evaporated under vacuum to give the expected product.