Reaction #1765

Reaction equation

6-bromo-2-(N,N-dipropylamino)-1,2,3,4-tetrahydronaphthalene

methyl acrylate

tri-ortho-tolylphosphine

triethylamine

→

expected product

Yield 28.5%

trans-3-[2-(N,N-dipropylamino)-1,2,3,4-tetrahydronaphth-6-yl]prop-2-enoic acid methyl ester

Yield 28.5%

Solvents

water

dimethylformamide

Conditions

Workup

1. 1
   TemperatureThe mixture is heated at 125°-130° C. for 3 h 30 min.
2. 2
   Temperaturecooled
3. 3
   Extractionextracted with ethyl acetate
4. 4
   Washwashed with a solution of LiCl

Procedure

3.1 g (0.01 mol) of 6-bromo-2-(N,N-dipropylamino)-1,2,3,4-tetrahydronaphthalene are dissolved in 50 ml of dimethylformamide. There are added in succession to that solution 0.94 g (0.011 mol) of methyl acrylate, 22.4 mg (0.1 mmol) of palladium acetate, 121 mg (0.4 mmol) of tri-ortho-tolylphosphine and 1.6 ml (0.011 mol) of triethylamine. The mixture is heated at 125°-130° C. for 3 h 30 min. with stirring, cooled, poured into 700 ml of water, extracted with ethyl acetate and washed with a solution of LiCl. After acid to base change, 0.9 g of the expected product is obtained.

Source