Reaction #1005981

Reaction equation

1,4-dimethylsulphonyl-2-butene

4-methoxybenzylamine

→

product

Yield 63.6%

1-(4-methoxybenzyl)-3-pyrroline

Yield 63.6%

Solvents

dichloromethane

Conditions

Workup

1. 1
   FiltrationThe solid was filtrated
2. 2
   Washthe filtrate was washed with water (2×30 ml)
3. 3
   Dryingdried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   OtherThe crude was purified by flash chromatography

Procedure

To a solution of 1,4-dimethylsulphonyl-2-butene (2.15 g, 11.64 mmol) in dichloromethane (40 ml), 4-methoxybenzylamine (6 ml, 44.24 mmol) was added dropwise and the solution was stirred 20 hours at r.t. The solid was filtrated and the filtrate was washed with water (2×30 ml), dried over Na2SO4, filtered and concentrated. The crude was purified by flash chromatography: silica gel, gradient hexane:ethyl acetate 3:1 to 1:1. to afforded the product (1.4 g, 63%) as yellow oil.

Source