Potassium Carbonate → 4-[3-[6-(3-Bromo-5-hydroxymethyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

Temperature

70 °C

To a solution of 4-[3-(6-bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (4.2 g, 8.9 mmol), 3-Bromo-5-hydroxymethyl-phenol (1.5 g, 7.4 mmol) in N,N-dimethylformamide (40 mL) and acetone (80 mL) was added potassium carbonate (10.2 g, 74.2 mmol) at room temperature. The resulting suspension was heated to 70° C. for 24 h. Then, the reaction mixture was cooled to room temperature and diluted with water and 10% aq. HCl. The organic compound was extracted into ethyl acetate and the combined organic extracts were washed with water and brine solution. The organic layers were dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The crude material was purified by column chromatography (Isco™ 120 g) with 0-50% ethyl acetate/hexanes as eluting solvents to afford the title compound (4.3 g, 99%) as a colorless oil. HR-ES(+) calcd for C30H41O7Br [M+Na]+ 615.1928, observed 615.1926.

1. temperatureThen, the reaction mixture was cooled to room temperature
2. extractionThe organic compound was extracted into ethyl acetate
3. washthe combined organic extracts were washed with water and brine solution
4. dry with materialThe organic layers were dried over anhydrous sodium sulfate
5. customthe solvent was removed under reduced pressure
6. customThe crude material was purified by column chromatography (Isco™ 120 g) with 0-50% ethyl acetate/hexanes
7. washas eluting solvents

ORD record

ord-f39d25e712b34f78b6300c2e3ffbd5fa

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08088936B2