S(=O)(O)[O-].[Na+].[CH:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.[C-:16]#[N:17].[Na+].COC(C)(C)C>O>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([CH:6]([OH:15])[C:16]#[N:17])=[CH:8][CH:9]=1Water (720 ml), sodium bisulfite (81 g, 0.775 mol, 1.2 equiv) and p-anisaldehyde (88 g, 0.646 mol, 1.0 equiv) are combined, warmed to 40° C. and stirred for 3 hrs. The slurry is cooled to 5° C., and sodium cyanide (35 g, 0.711 mol, 1.1 equiv) in 140 ml water is added. The reaction is stirred for 2 hrs. at 5° C., then warmed to room temperature, and methyl-t-butyl ether (MTBE) (400 ml) added. The layers are separated after a brief stir, and the aqueous phase re-extracted with MTBE (100 ml). The combined organic layers were dried (MgSO4), and concentrated to an oil, which was seeded to afford product: 69.5 g, 65.9%. The material can be recrystallized from toluene (3 ml per g substrate, heat to 35° C., cool to 5° C., 90% recovery).
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