Dimethylformamide → HCID 19363280, compound

2-(4-Methoxy-3-pentyloxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole (500 mg, 1.76 mmol) and DMF (8 ml) were mixed, and this solution was cooled to -60° C. n-Butyllithium (1.6M hexane solution, 2.42 ml, 3.87 mmol) was added and the mixture was stirred for 1 hour. Dimethyl disulfide (0.35 ml, 3.87 mmol) was added to this solution, and the mitxure was stirred at room temperature for 1 hour. Water (5 ml) was added, and the aqueous layer was extracted 3 times with ethyl acetate (10 ml). The organic layers were combined and concentrated under reduced pressure. A 3N hydrochloric acid (4 ml) was added to the obtained residue and the mixture was under heating for 3 hours. A 10N aqueous sodium hydroxide solution (4 ml) was added and the mixture was refluxed under heating for 2 hours. A concentrated hydrochloric acid (3 ml) was added to make the reaction mixture acidic, and the aqueous layer was extracted 4 times with ethyl acetate (20 ml). The organic layers were combined, washed 3 times with saturated brine (10 ml) and dried over anhydrous magnesium sulfate. The drying agent was filtered off and the filtrate was concentrated under reduced pressure. The obtained crude crystals were purified by washing with hexane to give 4-methoxy-2-methylthio-3-pentyloxybenzoic acid (370 mg, 74%) as pale-brown crystals.

1. additionwas added
2. stirringthe mitxure was stirred at room temperature for 1 hour
3. extractionthe aqueous layer was extracted 3 times with ethyl acetate (10 ml)
4. concentrationconcentrated under reduced pressure
5. additionA 3N hydrochloric acid (4 ml) was added to the obtained residue
6. temperatureunder heating for 3 hours
7. additionA 10N aqueous sodium hydroxide solution (4 ml) was added
8. temperaturethe mixture was refluxed
9. temperatureunder heating for 2 hours
10. additionA concentrated hydrochloric acid (3 ml) was added
11. extractionthe aqueous layer was extracted 4 times with ethyl acetate (20 ml)
12. washwashed 3 times with saturated brine (10 ml)
13. dry with materialdried over anhydrous magnesium sulfate
14. filtrationThe drying agent was filtered off
15. concentrationthe filtrate was concentrated under reduced pressure
16. customThe obtained crude crystals
17. customwere purified
18. washby washing with hexane

ORD record

ord-13789e45dd1c463698bce6faa46bd4a3

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06017919