Lithium hydride → HCID 59496799, Verbindung

To a solution of 4-[3-(6-bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (4.48 g, 9.5 mmol) and 5-bromo-benzene-1,3-diol (1.79 g, 9.47 mmol) in dimethylsulfoxide (30 mL) was added lithium hydride (160 mg, 20 mmol) at room temperature. The resulting suspension was stirred for 48 h and then the reaction mixture was diluted with water (100 mL). The organic compound was extracted into ethyl acetate (3×50 mL) and the combined organic extracts were washed with water (100 mL) and brine solution (100 mL). The organic layers were dried over anhydrous magnesium sulfate and filtration of the drying agent and concentration of the solvent under vacuum gave the crude product which was purified by using an ISCO 120 g column, eluting with 0-30% ethyl acetate in hexanes to afford 4-[3-[6-(3-bromo-5-hydroxy-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (2.73 g, 74%) as a white solid: ES(+)-HRMS m/e calcd for C29H39BrO7 (M+Na)+ 601.1771, found 601.1773.

1. extractionThe organic compound was extracted into ethyl acetate (3×50 mL)
2. washthe combined organic extracts were washed with water (100 mL) and brine solution (100 mL)
3. dry with materialThe organic layers were dried over anhydrous magnesium sulfate and filtration of the drying agent and concentration of the solvent under vacuum
4. customgave the crude product which
5. customwas purified
6. washeluting with 0-30% ethyl acetate in hexanes

ORD-Eintrag

ord-c9717640fc3046d8982624cd75bd0651

Quelldatensatz

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08088936B2