Reacción #1755460

Ecuación de reacción

3,5-dimethylbenzylmagnesium chloride

thiophene-2-carbaldehyde

lithium hexamethyldisilazane

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product

Rendimiento 30.0%

2-(3,5-Dimethyl-phenyl)-1-thien-2-yl-ethylamine

Rendimiento 30.0%

Disolventes

tetrahydrofuran

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added within 10 min
2. 2
   Temperaturato warm up to room temperature
3. 3
   OtroThis solution was quenched with aqueous potassium carbonate solution (5%)
4. 4
   Extracciónextracted with diethyl ether
5. 5
   OtroThe dried
6. 6
   Otroconcentrated ether extracts were purified by column chromatography

Procedimiento

A solution of thiophene-2-carbaldehyde (2.24 g) in anhydrous toluene was cooled to 0° C. under nitrogen inert-gas atmosphere and a solution of lithium hexamethyldisilazane (LiHMDS, 22 ml, 1.1 equiv.) was added via cannula over a 30 min period. The reaction mixture was allowed to warm up to room temperature for 2 h. After cooling to 0° C. again a solution of 3,5-dimethylbenzylmagnesium chloride (50 ml, ca. 1.5 equiv.) in tetrahydrofuran (THF) was added within 10 min and the reaction mixture allowed to warm up to room temperature and stirring continued for 3 h. This solution was quenched with aqueous potassium carbonate solution (5%) and extracted with diethyl ether. The dried and concentrated ether extracts were purified by column chromatography to give the product (1.4 g) as a yellowish oil in 30% yield.

Fuente