Reaction #6308

Reaction equation

Water

n-BuLi

4-(benzoxazol-2-yl)tolyltriphenylphosphonium bromide

3-(N-hydroxyhexyl-1,2,3,4-tetrahydroquinolin-6-yl)acrolein

→

1-(N-hydroxyhexyl-1,2,3,4-tetrahydroquinolin-6-yl)-4-(4-benzoxazol-ylphenyl)-1,3-butadiene

Solvents

toluene

toluene

Conditions

Workup

1. 1
   Otherthe solids are isolated by vacuum filtration
2. 2
   Washwashed with 60% ethanol/water
3. 3
   Otherdried under vacuum
4. 4
   OtherThe product is purified by recrystallization from benzene

Procedure

To a stirred mixture of 110 g (0.2 mole) of 4-(benzoxazol-2-yl)tolyltriphenylphosphonium bromide in toluene is added dropwise 0.2 mole of n-BuLi at room temperature. After 2 hours a solution of 28.7 g (0.1 mole) of 3-(N-hydroxyhexyl-1,2,3,4-tetrahydroquinolin-6-yl)acrolein in toluene is added dropwise to the mixture, and the reaction is stirred for 18 hours at room temperature. Water is added, and the solids are isolated by vacuum filtration, washed with 60% ethanol/water, and dried under vacuum. The product is purified by recrystallization from benzene.

Source