[CH2:1]=[C:2]([CH2:6][CH2:7][C:8]1[C:13]([O:14]C(=O)C)=[C:12]([CH3:18])[C:11]([CH3:19])=[C:10]([O:20]C(=O)C)[C:9]=1[CH3:24])[CH2:3][C:4]#[N:5].C[O-].[Na+].O.CCOCC>CO>[OH:20][C:10]1[C:11]([CH3:19])=[C:12]([CH3:18])[C:13]2[O:14][C:2]([CH3:1])([CH2:3][C:4]#[N:5])[CH2:6][CH2:7][C:8]=2[C:9]=1[CH3:24]A slurry of 500 mg (1.52 mmoles) of the mixture of E- and Z-3-methyl-5-(2,4,5-trimethyl-3,6-diacetyloxyphenyl)-3-pentenenitrile and 3-methylene-5-(2,4,5-trimethyl-3,6-diacetyloxy-phenyl)pentanenitrile in 5 ml of methanol was treated with 0.71 ml (3.34 mmoles) of a 4.7 M methanolic sodium methoxide solutiion. The resulting mixture was stirred at room temperature for 4.5 hr, then poured into 20 ml of water and worked-up with ether in the usual manner affording 345 mg (93%) of rac. 3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-acetonitrile as a tan solid.
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