Sodium Methoxide → 2-Hydroxy-1,3-oxazole-5-carboxylic acid

Ethyl 2-chlorooxazole-5-carboxylate (1.816 g, 10.34 mmol) was solubilised in MeCN (20 ml) and MeOH (20 ml). Sodium methoxide (9 ml, 25% solution in MeOH, 41.4 mmol) was added and the reaction mixture was heated at reflux overnight. The solvent was removed under reduced pressure and the crude product was dissolved in MeOH (20 ml) and 2M NaOH(aq) (20 ml) and stirred at RT overnight. The resulting mixture was acidified with 1M HCl and evaporated under reduced pressure. The residue was triturated with a minimal volume of 5M HCl and filtered. The solid was slurried with ice chips (approx. 10 ml), filtered, washed with water and dried under high vacuum to afford the title compound;

1. temperaturethe reaction mixture was heated
2. temperatureat reflux overnight
3. customThe solvent was removed under reduced pressure
4. dissolutionthe crude product was dissolved in MeOH (20 ml)
5. customevaporated under reduced pressure
6. customThe residue was triturated with a minimal volume of 5M HCl
7. filtrationfiltered
8. filtrationfiltered
9. washwashed with water
10. customdried under high vacuum

ORD record

ord-1c48b693924a4885aa7675d4694d221e

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409895B2