Pivaloyl chloride → N-(2-Chloro-6-(hydroxymethyl)phenyl)pivalamide

Participants

Reaction Steps

To the crude (2-amino-3-chlorophenyl)methanol (1.08 g, 6.88 mmol) in CH2Cl2(15 mL) was fast dropwise added trimethylacetyl chloride (0.89 mL, 7.23 mmol), followed by DIEA (2.4 mL, 13.8 mmol) at 0° C. 5 min later, the reaction mixture was stirred at room temperature for 1 hr. Normal aqueous work-up to afford the expected product as a white solid (1.58 g, 95% yield), which was pure enough to be used in next step; 1H NMR (400 MHz, CDCl3) δ ppm 1.30 (s, 9 H), 3.35 (s, 2 H), 4.36 (d, J=6.29 Hz, 1 H), 7.06-7.22 (m, J=7.81, 7.81 Hz, 1 H), 7.29-7.33 (m, 2 H), 7.58 (s, 1 H); Mass spec. 242.08 (MH+), Calc. for C12H16ClNO2 241.09.

Provenance & Evidence