Aluminium lithium hydride → 3,3,3-Trifluoro-2,2-dimethylpropanal

Participants

Reaction Conditions

Reaction Steps

To a 250-mL of three neck round-bottomed flask equipped with goose neck for nitrogen and for thermocouple was added lithium aluminium hydride, 1 M solution in Et2O (25.3 ml, 25.3 mmol) at 0° C. To the cooled mixture was added a solution of 3,3,3-trifluoro-N-methoxy-N,2,2-trimethylpropanamide (A294-1) (5.0325 g, 25.3 mmol) in Et2O (47.7 ml) dropwise over 35 min at 0° C. After the completion of the addition, the reaction mixture was further stirred at 0° C. After 2 h, the mixture was carefully quenched at 0° C. with water (0.96 mL), NaOH (15%, 0.96 mL) and water (2.88 mL) and the mixture was vigorously stirred for 40 min. The reaction mixture was diluted with Et2O (50 mL), treated with Na2SO4 and then filtered through a Celite pad, washed with Et2O (100 mL). The filtrate was concentrated in vacuo to provide 3,3,3-trifluoro-2,2-dimethylpropanal (A294-2) (3.2304 g, 23.06 mmol, 91% yield) as yellow liquid. 1H NMR (400 MHz, CDCl3) δ 9.69 (1H, d, J=1.4 Hz), 1.31 (6H, s).

Provenance & Evidence