Reaktion #4403

Reaktionsgleichung

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

Ausbeute 58.6%

Lösungsmittel

tetrahydrofuran

n-hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting precipitates
2. 2
   Filtrationwere collected by filtration
3. 3
   Waschenwashed with water
4. 4
   Sonstigerecrystallized from methanol

Vorschrift

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).

Quelle