Reaktion #567552

Reaktionsgleichung

Na(OAc)3BH

4-cyclohexenylaniline

methyl 4-formylbenzoate

acetic acid

→

4-[(4-cyclohex-1-enylphenylamino)methyl]benzoic acid methyl ester

Ausbeute 65.2%

Lösungsmittel

ethyl acetate

DCM

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGto stir at room temperature for 16 hours
2. 2
   Waschenwashed with aqueous sodium bicarbonate (3×), brine (2×)
3. 3
   Trocknendried over magnesium sulphate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   Sonstigeto give an orange solid
7. 7
   Wascheneluted with ethyl acetate:hexane (5:95)

Vorschrift

To a solution of 4-cyclohexenylaniline (3,40 g, 0.023 mol) and methyl 4-formylbenzoate (3.77 g, 0.023 mol) in DCM (50 ml) and methanol (15 ml) was added a catalytic amount of acetic acid. After stirring the solution for 3 hours, Na(OAc)3BH (24 g, 0.115 mol) was added. The reaction was allowed to stir at room temperature for 16 hours. The reaction mixture was diluted with ethyl acetate and washed with aqueous sodium bicarbonate (3×), brine (2×), dried over magnesium sulphate, filtered, and concentrated to give an orange solid. The crude product was introduced into a column of silica gel and eluted with ethyl acetate:hexane (5:95) to give 4-[(4-cyclohex-1-enylphenylamino)methyl]benzoic acid methyl ester (5 g, 0.015 mol).

Quelle