Methanol → Methyl 2-hydroxy-2-(2-methyl-1,3-thiazol-4-yl)acetate

Acetyl chloride 725 μL, 10.2 mmol) was dropped at 0° C. in methanol (10 mL). After 30 minutes, a solution of 2-(2-methyl-1,3-thiazol-4-yl)-2-[(trimethylsilyl)oxy]acetonitrile (15a) (3.93 mmol) in methanol (30 mL) was added at 0° C. to the reaction. The mixture was then warmed at room temperature for 20 hours and concentrated under vacuum. A saturated aqueous solution of sodium bicarbonate (20 mL) was added to the residue and extracted with dichloromethane (2×20 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (dichloromethane/ethyl acetate 80/20) to afford the desired hydroxyl-ester (15b) as a yellow oil (560 mg, 2.99 mmol, 90%).

1. concentrationconcentrated under vacuum
2. additionA saturated aqueous solution of sodium bicarbonate (20 mL) was added to the residue
3. extractionextracted with dichloromethane (2×20 mL)
4. washThe organic layer was washed with brine (10 mL)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. customevaporated under reduced pressure
8. customThe residue was purified by flash chromatography on silica gel (dichloromethane/ethyl acetate 80/20)

ORD record

ord-cb4c0929bd4343d9ba306016cda44cec

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238026B2