Reaktion #1012107

Reaktionsgleichung

EtOAc

ethyl benzoate

2-methylthiazole

n-BuLi

→

Intermediate 3

Ausbeute 17.0%

1-phenyl-2-(thiazol-2-yl)ethanone

Ausbeute 17.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture was stirred at room temperature overnight
2. 2
   Sonstigewere consumed
3. 3
   workup.ADDITIONwater was added
4. 4
   Sonstigeto quench
5. 5
   Sonstigethe reaction
6. 6
   Extraktionthe aqueous layer extracted with EtOAc (10 mL×3)
7. 7
   WaschenThe combined organic layer was washed with brine (10 mL)
8. 8
   Trocknendried over Na2SO4
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated
11. 11
    Sonstigepurified by column chromatography (PE:EtOAc=15:1)

Vorschrift

To a solution of 2-methylthiazole (500 mg, 5.1 mmol) in anhydrous THF (10 mL) at −78° C. under nitrogen was added dropwise n-BuLi (2.5 mol/L, 2.0 mL), after being stirred at this temperature for 1 hour, a solution of ethyl benzoate (1.1 g, 7.3 mmol) in anhydrous THF (5 mL) was added, and the reaction mixture was stirred at room temperature overnight. When TLC (PE:EtOAc=7:1) indicated that the starting materials were consumed, water was added to quench the reaction, and the aqueous layer extracted with EtOAc (10 mL×3). The combined organic layer was washed with brine (10 mL), dried over Na2SO4, filtered, concentrated, and purified by column chromatography (PE:EtOAc=15:1) to afford Intermediate 3 as a yellow oil (170 mg, yield: 17.0%).

Quelle