Zirconocene Chloride Hydride

• N,N-Diethylnicotinamide [D0514]
• Ziconocene Chloride Hydride [Z0010]
• THF

Zirconocene chloride hydride (0.43 g, 1.68 mmol) was added to a reaction vessel and dried in vacuo for 3 hours. Then, a THF solution (4.1 mL) of N,N-diethylnicotinamide (200 mg, 1.12 mmol) was added under argon atmosphere and the reaction mixture was stirred at room temperature for 30 minutes. The mixture was puried by chromatography on silica gel (hexane:ethyl acetate = 2:1) to give nicotinaldehyde as a brown oil (80.0 mg, 0.07 mmol, 60% yield).

The reaction solution was monitored by TLC (hexane:ethyl acetate = 1:1) and UPLC.
The reaction vessel was dried up before use.

Nicotinaldehyde

¹H NMR (400 MHz, DNSO-d₆); δ 10.09 (s, 1H), 9.07 (d, J = 1.4 Hz, 1H), 8.84 (dd, J = 5.0 Hz, 1.8 Hz, 1H), 8.23 (dt, J = 7.8 Hz, 2.1 Hz, 1H), 7.62 (dd, J = 8.5 Hz, 2.1 Hz, 1H).

• Mild and Selective Hydrozirconation of Amides to Aldehydes Using Cp₂Zr(H)Cl: Scope and Mechanistic Insight
  • J. T. Spletstoser, J. M. White, A. R. Tunoori, G. I. Georg. J. Am. Chem. Soc. 2007,129, 3408.