Hydrochloric Acid → HCID 20743446, compound

Temperature

0 °C

A solution of sodium bis(trimethylsilyl)amide (36 mL, 1M) was diluted with THF (60 mL) and cooled to 0° C. 2-Fluoro-4-methylpyridine (2.0 g, 18 mmol) was then added and after 45 min. at 0° C. ethyl benzoate (3.24 g, 21 mmol) was added dropwise. Stirring was continued for 45 min. and the solution then poured into 2M HCl (100 mL) cooled to 0° C. After thorough mixing, the solution was basified to pH9 with 5M NaOH, and the product extracted into ether (3×30 mL). The ethereal layers were combined and washed with brine (1×30 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was dissolved in a minimum of dichloromethane and precipitated by addition of pet. spirit. The solid was collected and washed with cold pet. spirit to afford the pure product as a pale brown solid (2.8 g, 72%).

1. additionwas added dropwise
2. temperaturecooled to 0° C
3. extractionthe product extracted into ether (3×30 mL)
4. washwashed with brine (1×30 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated under reduced pressure
7. dissolutionThe residue was dissolved in a minimum of dichloromethane
8. customprecipitated by addition of pet
9. customThe solid was collected
10. washwashed with cold pet

ORD record

ord-c5d1a55ad0aa45bb994b9661d2bec29a

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07593820B2