Reaction #65712

Reaction equation

benzaldehyde

[1-(1,2,3,4-tetrahydro-1,4,4-trimethyl-6-quinolinyl)ethyl]triphenylphosphonium bromide

n-butyllithium

→

1,2,3,4-tetrahydro-1,4,4-trimethyl-6-(α-methylstyryl)quinoline

Yield 44.0%

Solvents

hexane

tetrahydrofuran

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for an additional 1 hour
2. 2
   OtherAfter working-up in analogy to Example 49 and recrystallization from hexane

Procedure

5.1 g of [1-(1,2,3,4-tetrahydro-1,4,4-trimethyl-6-quinolinyl)ethyl]triphenylphosphonium bromide were suspended in 40 ml of tetrahydrofuran and treated at -20° C. with 5.9 ml of a 1.6 molar solution of n-butyllithium in hexane. After stirring at -20° C. for 1 hour, 1 g of benzaldehyde was added thereto and the mixture was stirred at room temperature for an additional 1 hour. After working-up in analogy to Example 49 and recrystallization from hexane, there were obtained 1.2 g of 1,2,3,4-tetrahydro-1,4,4-trimethyl-6-(α-methylstyryl)quinoline, melting point 69°-71° C.

Source