[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][C:16]#[N:17])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Li].[CH3:19]C(NC(C)C)C.IC>C1COCC1>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([CH3:19])[C:16]#[N:17])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1A mixture of 3-(cyclopentyloxy)-4-methoxybenzeneacetonitrile (20 g) in THF (200 ml) was stirred at −78° C. under a N2 flow. N-(1-methylethyl)-2-propanamine lithium salt (45 ml) was added dropwise and the resulting mixture was stirred for 30 minutes at −78° C. Iodomethane (13.5 g) was added dropwise and the resulting reaction mixture was allowed to warm to RT. The reaction mixture was stirred for 2 hours. The mixture was quenched with a saturated aqueous NH4Cl solution (200 ml) and was extracted with CH2Cl2(3×100 ml). The separated organic layer was dried (MgSO4), filtered and the solvent was evaporated, yielding 17.7 g (100% ) of (±)-3-(cyclopentyloxy)-4-methoxy-α-methylbenzeneacetonitrile (interm. 8).
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