Reaktion #1927610

Reaktionsgleichung

ammonium chloride

n-butyllithium n-hexane

7-(2-formylaminoethyl)thioimidazo[5,1-b]thiazole

n-butyllithium n-hexane

tri-n-butylstannyl chloride

Tri-n-butylstannyl chloride

→

7-(2-Formylaminoethyl)thio-2-(tri-n-butylstannyl)imidazo[5,1-b]thiazole

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred for 20 min
2. 2
   workup.ADDITIONwere added
3. 3
   Extraktionthe mixture was extracted with ethyl acetate
4. 4
   Waschenby washing with brine
5. 5
   TrocknenThe organic layer was dried over anhydrous magnesium sulfate
6. 6
   SonstigeThe solvent was removed by distillation
7. 7
   Sonstigethe residue was purified by column chromatography on silica gel (ethyl acetate only to dichloromethane
8. 8
   Sonstigemethanol=20:1) to prepare 1.615 g of the title compound

Vorschrift

A 1.6 N n-butyllithium/n-hexane solution (11.7 ml) was added to a solution of 1.19 g of 7-(2-formylaminoethyl)thioimidazo[5,1-b]thiazole in 50 ml of THF at −55° C. under an argon atmosphere. The mixture was stirred at that temperature for 10 min. Tri-n-butylstannyl chloride (2.24 ml) was added thereto, and the mixture was stirred for 20 min. The temperature of the reaction solution was raised to −30° C. over a period of one hr, during which time 3.34 ml of a 1.6 N n-butyllithium/n-hexane solution and 2.4 ml of tri-n-butylstannyl chloride were added. An aqueous ammonium chloride solution was added to the reaction solution, and the mixture was extracted with ethyl acetate, followed by washing with brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation, and the residue was purified by column chromatography on silica gel (ethyl acetate only to dichloromethane:methanol=20:1) to prepare 1.615 g of the title compound.

Quelle