Reaktion #1001486

Reaktionsgleichung

2-{[4-(2-Hydroxyethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

2-{[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

4-bromophenol

triphenylphosphine

diisopropyl diazodicarboxylate

→

title compound

Ausbeute 74.4%

2-({4-[2-(4-bromophenoxy)ethyl]-1,3-thiazol-2-yl}thio)-2-methylpropionic acid tert-butyl ester

Ausbeute 74.4%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   EinengenThe reaction mixture was concentrated under reduced pressure
3. 3
   Sonstigethe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=10:1 to 5:1)

Vorschrift

2-{[4-(2-Hydroxyethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (3.077 g) synthesized in Example 4 and 4-bromophenol (1.75 g) were dissolved in tetrahydrofuran (50 mL), triphenylphosphine (3.20 g) and diisopropyl diazodicarboxylate (40% toluene solution, 6.54 ml) were added under ice-cooling, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=10:1 to 5:1) to give the title compound (3.45 g) as a colorless oil.

Quelle