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

Temperature

-70 °C

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.

1. customtransferred via a cannula to a flask
2. stirringthe mixture was stirred at 25° C. for 30 minutes
3. customThe phases were split
4. extractionthe aqueous phase was extracted with 5 mL of CH2Cl2
5. washThe combined organic phase was washed with brine
6. dry with materialdried over MgSO4

ORD record

ord-a753f005eeff402290dea6130aea57a9

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07476762B2