Water → HCID 21927816, compound

Participants

Reaction Steps

Trifluoromethanesulfonic anhydride (5.4 mL; 31.8 mmoles) was added to an ice cooled solution of methyl 5-amino-3,3-dimethyl-5-oxopentanoate (5.00 g; 28.9 mmoles) in methylene chloride (250 mL) and triethylamine (8 mL; 57.8 mmoles), under nitrogen while keeping the temperature below 5° C. The reaction mixture was allowed to warm to room temperature and stirred for 30 minutes. Water (125 mL) was added and the phases were separated. The aqueous phase was extracted with methylene chloride (100 mL). The organic phases were combined, washed with saturated aqueous sodium chloride solution and dried over sodium sulfate. The solution was filtered and the solvent was removed under vacuum to give the product, methyl 4-cyano-3,3-dimethylbutanoate (3.1 g; 69%). 1H NMR (400 MHz) DMSO-d6 δ 3.60 (3H, s), 2.61 (2H, s), 2.35 (2H, s), 1.07 (6H, s).

Provenance & Evidence