Water → N-(3-acetylphenyl)-2,2-dimethylpropanamide

Participants

Reaction Steps

To a stirred solution of 3-aminoacetophenone (1.0 g, 7.4 mmol) in chloroform cooled to 0° C. was added triethylamine dropwise (1.44 g, 14.2 mmol). The mixture was stirred for 15 min at this temperature and then pivaloyl chloride (0.83 g, 7.4 mmol) was added dropwise and the mixture was stirred overnight. Water was added and the aqueous layer was extracted with DCM. The collected organic extracts were washed with sat. aq. NaHCO3 and brine, dried over anhydrous MgSO4, and filtered. The solvent was evaporated under reduced pressure to afford 8z as a white solid (1.29 g, 80%). Mp 130-133° C. 1H NMR (600 MHz, CDCl3): δ 8.07 (t, J=1.8 Hz, 1H), 7.90-7.88 (m, 1H), 7.76 (br s, 1H), 7.65-7.63 (m, 1H), 7.37 (t, J=1.8 Hz 1H), 2.57 (s, 3H), 1.31 (s, 9H). 13C NMR (150 MHz, CDCl3): δ 198.2, 177.2, 138.8, 137.7, 129.3, 124.9, 124.1, 119.7, 39.8, 27.6, 26.8.

Provenance & Evidence