Water → 2-hydroxy-N,N,2-trimethylbut-3-ynamide
Reaction equation
[CH3:1][N:2]([CH3:8])[C:3](=[O:7])C(=O)C.[C:9]([Mg]Br)#[CH:10].[OH2:13].[CH2:14]1COC[CH2:15]1>>[OH:13][C:9]([CH3:10])([C:14]#[CH:15])[C:3]([N:2]([CH3:8])[CH3:1])=[O:7]Participants
Procedure
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)+.
Workup
- concentrationthe resulting slurry concentrated in vacuo
- customThe residue was slurried in DCM (50 mL) with sonication for 5 min.
- filtrationthe mixture filtered
- additionre-suspension of the filter cake in water (10 mL)
- extractionthe resulting hazy solution re-extracted with DCM (30 mL)
- extractionThe DCM extract
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationthe filtrate concentrated in vacuo
Sources & evidence
- ORD record
- ord-2d689df059a64ab3b9d6847c02444989
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901313B2
Reaction notes
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