Potassium Carbonate → 2-[1-Methoxy-1-[3-(1,2-dihydro-1-methyl-2-oxoquinolin-3-ylmethoxy)phenyl]propyl]thiazole

A mixture of 2-[1-(3-hydroxyphenyl)-1-methoxypropyl]thiazole (0.5 g, 2 mmol), 3-bromomethyl-1,2-dihydro-1-methylquinolin-2-one (0.5 g, 2 mmol), potassium carbonate (0.35 g, 2.5 mmol) and dimethylformamide (3 ml) was stirred at ambient temperature for 48 hours. The mixture was filtered, the filtrate was added to water (30 ml) and the mixture was extracted with ethyl acetate (3×15 ml). The organic extracts were combined, washed with a dilute aqueous sodium hydroxide solution and with a saturated sodium chloride solution, dried (Na2SO4) and evaporated. The residue was purified by column chromatography eluting with toluene/ethyl acetate (7/3 v/v) to give 2-[1-methoxy-1-[3-(1,2-dihydro-1-methyl-2-oxoquinolin-3-ylmethoxy)-phenyl]propyl]thiazole (0.84 g, 100%), m.p. 123°-125° C.

1. filtrationThe mixture was filtered
2. additionthe filtrate was added to water (30 ml)
3. extractionthe mixture was extracted with ethyl acetate (3×15 ml)
4. washwashed with a dilute aqueous sodium hydroxide solution and with a saturated sodium chloride solution
5. dry with materialdried (Na2SO4)
6. customevaporated
7. customThe residue was purified by column chromatography
8. washeluting with toluene/ethyl acetate (7/3 v/v)

ORDレコード

ord-c7dda33bfee5481a9251ceb52bc567df

出典データセット

uspto-grants-1994_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05283245