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

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.

1. filtrationThe crude in dichloromethane was filtered through silica gel
2. additionCelite was added to the remaining black viscous oil from the reaction mixture until the viscous oil
3. customall absorbed to the celite
4. additionDichloromethane was added to this slurry
5. filtrationthe dichloromethane solution was filtered through silica gel
6. customDichloromethane was removed at reduced pressure (80 Torr)
7. customto give a pale yellow crude
8. distillationDistillation
9. customremoved residue dichloromethane

ORD record

ord-79c9cc98da1d4669891bea3364cf7f71

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08314246B2