Ethyl 2-hydroxyisobutyrate → 2-Ethoxy-5-(methanesulfonyl)pyridine

Temperature

80 °C

A mixture of ethyl 2-hydroxyisobutyrate (0.41 mL, 3.0 mmol), 2,5-bis(methyl sulfonyl)pyridine (J. Heterocycl. Chem. 1985, 22, 1583) (0.70 g, 3.0 mmol) and sodium hydride (60% dispersion in mineral oil, 0.14 g, 3.6 mmol) in 30 mL of anhydrous DMF was heated at 80° C. overnight. The reaction mixture was cooled to room temperature, and was partitioned between saturated aqueous ammonium chloride (200 mL) and ether (200 mL). The organic layer was separated and was washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated to dryness, and the residue was purified by flash column chromatography on silica gel eluting with 0 to 80% ethyl acetate in hexane to give the title compound as a 1:1 mixture with 2-ethoxy-5-methylsulfonylpyridine. LC-MS: m/e 288 (M+H)+ (0.70 min).

1. temperatureThe reaction mixture was cooled to room temperature
2. customwas partitioned between saturated aqueous ammonium chloride (200 mL) and ether (200 mL)
3. customThe organic layer was separated
4. washwas washed with water and brine
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated to dryness
8. customthe residue was purified by flash column chromatography on silica gel eluting with 0 to 80% ethyl acetate in hexane

ORD record

ord-731230f7622f4eb8992ff869e9460dec

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07550489B2