Reacción #4403

Ecuación de reacción

dry ice

8-benzyloxy-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine

n-butyllithium

acetic acid

→

8-benzyloxy-3-(3-carboxy-2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine

Rendimiento 58.6%

Disolventes

tetrahydrofuran

n-hexane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting precipitates
2. 2
   Filtraciónwere collected by filtration
3. 3
   Lavadowashed with water
4. 4
   Otrorecrystallized from methanol

Procedimiento

To a solution of 8-benzyloxy-3-(2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine (1 g) in tetrahydrofuran (10 ml) was added dropwise 10% solution of n-butyllithium in n-hexane (2.09 ml) at -60° C. under a nitrogen atmosphere. After being stirred for 10 minutes the solution was treated with dry ice (1.4 g), allowed to warm to room temperature, and acidified with diluted acetic acid. The resulting precipitates were collected by filtration, washed with water, and recrystallized from methanol to give 8-benzyloxy-3-(3-carboxy-2-propynyloxymethyl)-2-methylimidazo[1,2-a]pyridine (0.67 g).

Fuente