Methyl 3-hydroxypivalate → Methyl 2,2-dimethyl-3-oxopropanoate

Participants

Reaction Steps

3-Hydroxy-2,2-dimethyl-propionic acid methyl ester (15 g, 113 mmol) in 200 mL dichloromethane was cooled to 0° C. Pyridinium chlorochromate (43 g, 200 mmol) was added. The mixture was slowly warmed to room temperature and stirred 24 h. The crude in dichloromethane was filtered through silica gel. Celite was added to the remaining black viscous oil from the reaction mixture until the viscous oil is all absorbed to the celite. Dichloromethane was added to this slurry and the dichloromethane solution was filtered through silica gel. Dichloromethane was removed at reduced pressure (80 Torr) to give a pale yellow crude. Distillation removed residue dichloromethane and obtained 2,2-dimethyl-3-oxo-propionic acid methyl ester as a colorless oil (7 g, 48% yield). 1H NMR (300 MHz, CDCl3, δ): 9.60 (s, 1H); 3.70 (s, 3H); 1.29 (s, 6H). 13C NMR (75 MHz, CDCl3, δ): 199.1, 173.2, 53.9, 52.6, 19.7. IR (NaCl, thin film): 2988, 2958, 1726, 1468, 1278, 1151, 866.

Provenance & Evidence