Hydrochloric Acid → 4,4,4-Trifluoro-2-(2,2,2-trifluoroethyl)butanal

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Reaction Conditions

Reaction Steps

To a solution of 4,4,4-trifluoro-N-methoxy-N-methyl-2-(2,2,2-trifluoroethyl)-butyramide (2.67 g, 10 mmol) in CH2Cl2 (10 mL) was added diisobutylaluminum hydride (2.9 mL, 16 mmol) over 10 minutes at −70° C. The reaction mixture was stirred at −70° C. for 40 minutes, then transferred via a cannula to a flask containing 30 mL of 2N HCl at 0° C. Ten mL of concentrated HCl was added, and the mixture was stirred at 25° C. for 30 minutes. The phases were split and the aqueous phase was extracted with 5 mL of CH2Cl2. The combined organic phase was washed with brine and dried over MgSO4. NMR analysis of the solution using an internal standard indicated formation of the title product in 65% yield. The solution was used as such for further transformations.

Provenance & Evidence