[H-].[Na+].[I:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O.[NH4+].[Cl-].Cl.[C:15]([O:18][CH2:19][CH3:20])(=[O:17])[CH3:16]>C1COCC1.O>[I:3][C:4]1[CH:5]=[C:6](/[CH:7]=[CH:16]/[C:15]([O:18][CH2:19][CH3:20])=[O:17])[CH:9]=[CH:10][CH:11]=1
To a suspension of NaH (60% dispersion in mineral oil) (120 mg, 3.0 mmol) in THF (20 mL) was added triethyl phosphonoacetate (436 μL, 2.2 mmol) dropwise. 3-iodo-benzaldehyde (465 mg, 2.0 mmol) was added after the bubbling has stopped. The reaction mixture was stirred at room temperature for 15 minutes. Solid NH4Cl was added, followed by 1N HCl to quench the reaction. The mixture was taken up in ethyl acetate and water. The organic phase was washed with aqueous NaHCO3, brine, dried (MgSO4), filtered and concentrated under reduced pressure and purified by flash chromatography on silica gel with hexane/ethyl acetate (4:1) to provide the titled compound (605 mg).
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