Potassium Carbonate → HCID 86719322, Verbindung

Temperatur

80 °C

A mixture of 2-[(4-fluorophenyl)amino]ethan-1-ol (1.3 g, 8.39 mmol), methyl 4-bromobutyrate (2.28 g, 12.58 mmol), potassium carbonate (2.31 g, 16.77 mmol), and anhydrous N,N-dimethylformamide (6 mL) was added to a 50 mL RBF with a magnetic stirring bar. The mixture was allowed to stir at 80° C. for 16 hours. Progress of the reaction was monitored by TLC using ethyl acetate:hexanes (1:1) (Rf product=0.5). Another aliquot of methyl 4-bromobutyrate (0.76 g, 4.20 mmol) was added and this was allowed to stir at 80° C. for 20 hours, until 2-[(4-fluorophenyl)amino]ethan-1-ol was consumed by TLC analysis. The reaction was partitioned using ethyl acetate (50 mL) and water (15 mL). The aqueous layer was extracted with ethyl acetate (20 mL). The combined organic layer was washed with saturated aqueous NaCl (3×10 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography using a gradient elution of 20-100% ethyl acetate in hexanes to afford the title compound as an oil (1.1 g, 52% yield).

1. additionwas added to a 50 mL RBF with a magnetic stirring bar
2. customwas consumed by TLC analysis
3. customThe reaction was partitioned
4. extractionThe aqueous layer was extracted with ethyl acetate (20 mL)
5. washThe combined organic layer was washed with saturated aqueous NaCl (3×10 mL)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe crude material was purified by silica gel column chromatography
10. washa gradient elution of 20-100% ethyl acetate in hexanes

ORD-Eintrag

ord-dac765aafb60407b91704a01787b5b3b

Quelldatensatz

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09163027B2