[CH3:1][O-:2].[Na+].[CH3:4][O:5][C:6]1[CH:15]=[C:14]([CH:16]=[C:17]([CH2:20][O:21][CH3:22])[C:18]#[N:19])[C:9]2[CH:10]=[CH:11][CH2:12][O:13][C:8]=2[C:7]=1[O:23][CH3:24]>CO.O>[CH3:4][O:5][C:6]1[CH:15]=[C:14]([CH2:16][CH:17]([CH:20]([O:2][CH3:1])[O:21][CH3:22])[C:18]#[N:19])[C:9]2[CH:10]=[CH:11][CH2:12][O:13][C:8]=2[C:7]=1[O:23][CH3:24]A mixture of sodium methoxide (8.86 g, 0.164 mole), and 3-(7,8-dimethoxy-2H-1-benzopyran-5-yl)-2-methoxymethylpropenenitrile (Example 37A, 23.1 g, 0.080 mole) in methanol (60 mL) was heated at reflux for 24 hr, allowed to cool and diluted with water (200 mL). The resultant mixture was extracted with toluene (1×200 mL and 2×100 mL). The combined toluene portions were extracted with water (3×100 mL) and dried over magnesium sulfate. The toluene solution was concentrated leaving a brown oil which was distilled under reduced pressure to give 15.9 g (62%) of a yellow oil which was used without further purification.
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