2,6-Lutidine → HCID 77231060, compound

To a solution of the product of Step 1 (1.73 g, 10 mmol) in 1,4-dioxane (75 mL) and water (25 mL) was added osmium tetroxide (4 wt % in water, 0.392 mL, 0.05 mmol), 2,6-lutidine (2.329 mL, 20 mmol), and sodium periodate (8.56 g, 40 mmol). After stirring for 14 hours, a large amount of white precipitate had built up. The reaction mixture was then partitioned between diethyl ether (100 mL) and water (25 mL). The layers were separated and the aqueous layer was extracted with diethyl ether (2×50 mL). The combined organic layers were washed with saturated aqueous sodium bicarbonate solution (50 mL) and brine (50 mL), dried over sodium sulfate, filtered, and concentrated to provide methyl 2-methyl-2-(2-oxopropoxy)propanoate as a brown oil (1.74 g, 10 mmol), which was used without further purification. 1H NMR (500 MHz, CDCl3) δ 4.02 (s, 2H), 3.73 (s, 3H), 2.22 (s, 3H), 1.48 (s, 6H).

1. customThe reaction mixture was then partitioned between diethyl ether (100 mL) and water (25 mL)
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with diethyl ether (2×50 mL)
4. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate solution (50 mL) and brine (50 mL)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-efbf17909591487c81e6e0033eb1ee40

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759366B2