Tetrahydrofuran → (2E)-3-[4-(tert-Butyl)phenyl]-N-[3-(2-hydroxyethoxy)phenyl]prop-2-enamide

To a round-bottomed flask, equipped with magnetic stirring and reflux condenser, was added (2E)-3-[4-(tert-butyl)phenyl]-N-(3-hydroxyphenyl)prop-2-enamide, Example 23, (200 mg, 0.68 mmol), THF (10 mL), 2-bromoethanol (200 uL, 2.80 mmol, Aldrich) and 5 N NaOH (10 mL). The reaction mixture was stirred at reflux for 5 h. After allowing to cool to 25° C., the mixture was extracted with EtOAc (20 mL). The organic extract was washed with water (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (2:1 hexane:EtOAc) provided the title product as a colorless oil. MS (ESI, pos. ion) m/z: 340 (M+1).

1. customTo a round-bottomed flask, equipped
2. temperaturereflux condenser
3. stirringThe reaction mixture was stirred
4. temperatureat reflux for 5 h
5. extractionthe mixture was extracted with EtOAc (20 mL)
6. extractionThe organic extract
7. washwas washed with water (20 mL)
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customPurification by silica gel chromatography (2:1 hexane:EtOAc)

ORD-Eintrag

ord-defbf4eefb3e4831a3355b8357f852e6

Quelldatensatz

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07579347B2