Dimethyl Sulfoxide → Methyl 2,2-dimethyl-3-oxopropanoate

Temperature

0 °C

DMSO (22.0 mL, 303 mmol, 4.00 equiv) was added to a pre-cooled solution of oxalyl chloride (13.7 mL, 151 mmol, 2.00 equiv) in dichloromethane (40 mL) at −78° C., and the resulting mixture was stirred for 15 minutes before a solution of methyl 3-hydroxy-2,2-dimethylpropanoate (10.0 g, 75.7 mmol, 1 equiv) in dichloromethane (100 mL) was added. The reaction mixture was stirred for 1 hour, then triethylamine (52.7 mL, 378 mmol, 5.00 equiv) was added. The mixture was warmed to 0° C. and held for 30 minutes, then concentrated to a volume of ca 50 mL. The residue was partitioned between aqueous saturated sodium bicarbonate solution (200 mL) and ethyl acetate (200 mL). The organic layer was dried over sodium sulfate and concentrated on a rotorary evaporator without using heat (product is volatile) to provide methyl 2,2-dimethyl-3-oxopropanoate (29-1) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 9.66 (s, 1H), 3.76 (s, 3M), 1.36 (s, 6H).

1. additionwas added
2. waitheld for 30 minutes
3. concentrationconcentrated to a volume of ca 50 mL
4. customThe residue was partitioned between aqueous saturated sodium bicarbonate solution (200 mL) and ethyl acetate (200 mL)
5. dry with materialThe organic layer was dried over sodium sulfate
6. concentrationconcentrated on a rotorary evaporator
7. temperaturewithout using heat (product is volatile)

ORD record

ord-3079bb96502d4d3aa00671099640badd

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07348440B2