Water → 2-hydroxy-N,N,2-trimethylbut-3-ynamide

Participants

Reaction Steps

To a solution of N,N-dimethyl-2-oxopropanamide (413 mg, 3.59 mmol) in dry THF (10 mL) at 0° C. under an atmosphere of nitrogen was introduced ethynylmagnesium bromide (10 mL of a 0.5M solution in THF, 5.00 mmol) dropwise over 10 minutes. After warming to RT for 1 hr, water was introduced dropwise until gas evolution ceased and the resulting slurry concentrated in vacuo. The residue was slurried in DCM (50 mL) with sonication for 5 min. and the mixture filtered. Following re-suspension of the filter cake in water (10 mL), the pH was adjusted to 2 with 1M aqueous hydrochloric acid and the resulting hazy solution re-extracted with DCM (30 mL). The DCM extract was combined with the DCM filtrate, dried (Na2SO4), filtered and the filtrate concentrated in vacuo to furnish the crude title compound as a brown oil: 1H NMR (500 MHz, CDCl3) delta 1.68 (3H, s), 2.64 (1H, s), 3.08 (3H, s), 3.31 (3H, s), 5.25 (1H, br. s); LC-MS: m/z=+141.95 (M+H)+.

Provenance & Evidence