Sodium Hydroxide → HCID 14801708, compound

A solution of 1.55 g (13.2 mmol) of methyl 2-hydroxy-2-methylpropionate in 4 ml of dimethylformamide was added during 1 hour to a stirred suspension of 0.53 g (13.2 mmol) of a 60% sodium hydride dispersion in mineral oil in 8 ml of dry dimethylformamide. The solution was stirred at room temperature for 1 hour and was then added slowly to a solution of 2 g (9.4 mmol) of 2-(4-chlorophenyl)-4-chloromethyl-oxazole in 4 ml of dry dimethylformamide at 0° C. under an argon atmosphere. The mixture was stirred at room temperature overnight and 2 ml of saturated aqueous ammonium chloride were then added. The majority of the solvent was removed by evaporation under reduced pressure and the residue was partitioned between 100 ml of diethyl ether and 100 ml of water. The organic phase was separated, washed with 100 ml of water and dried over magnesium sulphate. The organic solution was filtered and evaporated to give 2.7 g of a crude solid. This solid was dissolved in 100 ml of ethanol and 0.4 g (10 mmol) of sodium hydroxide in 5 ml of water was added. The solution was heated at reflux for 1 hour, cooled and the majority of the solvent was removed under reduced pressure. The solid residue was dissolved in 400 ml of water and extracted twice with 100 ml of diethyl ether each time. The aqueous phase was acidified to pH 2 with concentrated hydrochloric acid and extracted three times with 100 ml of dichloromethane each time. The combined dichloromethane extracts were dried over magnesium sulphate, filtered and evaporated to give a solid which was recrystallized from ethyl acetate. There were obtained 1.6 g (57%) of 2-[[2-(4-chlorophenyl)-4-oxazolyl]methoxy]-2-methylpropionic acid of melting point 144.5°-145° C.

1. stirringThe mixture was stirred at room temperature overnight
2. customThe majority of the solvent was removed by evaporation under reduced pressure
3. customthe residue was partitioned between 100 ml of diethyl ether and 100 ml of water
4. customThe organic phase was separated
5. washwashed with 100 ml of water
6. dry with materialdried over magnesium sulphate
7. filtrationThe organic solution was filtered
8. customevaporated
9. customto give 2.7 g of a crude solid
10. temperatureThe solution was heated
11. temperatureat reflux for 1 hour
12. temperaturecooled
13. customthe majority of the solvent was removed under reduced pressure
14. dissolutionThe solid residue was dissolved in 400 ml of water
15. extractionextracted twice with 100 ml of diethyl ether each time
16. extractionextracted three times with 100 ml of dichloromethane each time
17. dry with materialThe combined dichloromethane extracts were dried over magnesium sulphate
18. filtrationfiltered
19. customevaporated
20. customto give a solid which
21. customwas recrystallized from ethyl acetate

ORD record

ord-6cea3df60e7a4f17b14fe5b441e9d57a

Source dataset

uspto-grants-1988_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04774253