[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:12]([OH:18])=[C:13]([C:16]#[N:17])[C:14]#[N:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].[C:19](=O)(O)[O-].[Na+].O1CCOCC1.COS(OC)(=O)=O>O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:12]([O:18][CH3:19])=[C:13]([C:14]#[N:15])[C:16]#[N:17])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]2-((3-ethoxy-4-methoxyphenyl)(hydroxy)methylene)malononitrile (25.5 mmol) and sodium bicarbonate (17 g, 204 mmol) were combined in a solution of 1,4-dioxane (48 mL) and water (8 mL). Dimethylsulphate (17 mL, 178 mmol) was slowly added and the reaction was heated to 80-90° C. for 2 hours. The reaction was cooled to RT, water was added, and the aqueous phase extracted three times with EtOAc (200 mL). The organic phases were combined, dried with MgSO4, and filtered to give a red oil. The oil was purified by silica gel chromatography (10% EtOAc/Hexanes, Rf˜0.1) to give a white solid (3.59 g, 54.5% yield over three steps). ESI-MS (M+H)+ m/z calcd 259.1, found 259.0.
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