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Nitrile to Aldehyde

(DIBAL-H)







Examples:


Example 1



To a 100 mL, 3-necked, RBF was added the SM (0.50 g, 1.711 mmol) and DCM (9 mL). The mixture was purged with N2 and cooled to -64 C. Under N2 atmsophere, was added DIBAL-H (1.0M in hexane, 2.6 mL, 2.6 mmol). The mixture was stirred at -64 C for 2 h. While maintaining the temp below -65 C, the mixture was quenched with the careful dropwise addition of MeOH (1.4 mL, 34.2 mmol), followed by sat. Rochelle salt solution (5 mL). The mixture was allowed to warm to RT and stir for 30 min. The mixture was diluted with H2O and DCM. The layers were separated and the aq layer was further extracted with DCM. The combined organics were washed with brine, dried (MgSO4), and concentrated to provide the product as a colorless oil. [0.517 g, crude] [WO2015129926, page 111]