反応 #49709

反応方程式

4-iodoaniline

dichloroethane

2-octanone

sodium

→

N-(4'-iodophenyl)-2-aminooctane

収率 88.0%

溶媒

acetic acid

反応条件

後処理

1. 1
   workup.STIRRINGThe reaction was stirred under an N2 atmosphere for 16 hrs
2. 2
   その他At the end of this period the reaction was quenched by the careful addition of a solution of saturated aqueous ammonium chloride (100 ml)
3. 3
   workup.STIRRINGAfter stirring for 0.5 hr
4. 4
   workup.ADDITIONthe reaction was poured over ether (250 ml)
5. 5
   その他the layers were separated
6. 6
   洗浄The ether layer was washed with saturated aqueous ammonium chloride (100 ml)
7. 7
   乾燥dried (Na2SO4)
8. 8
   ろ過filtered
9. 9
   その他evaporated in vacuo

実験手順

A flask containing 4-iodoaniline (11.0 g, 50.2 retool) was charged with dry dichloroethane (125 ml), 2-octanone (7.9 ml, 50.0 retool) and sodium triacetexyborohydride (13.8 g, 65 retool). After stirring for 10 minutes, acetic acid (2.9 ml, 50.7 retool) was added via syringe over a 5 minute period. The reaction was stirred under an N2 atmosphere for 16 hrs. At the end of this period the reaction was quenched by the careful addition of a solution of saturated aqueous ammonium chloride (100 ml). After stirring for 0.5 hr, the reaction was poured over ether (250 ml) and the layers were separated. The ether layer was washed with saturated aqueous ammonium chloride (100 ml), dried (Na2SO4), filtered and evaporated in vacuo. Flash column chromatography (silica, 1:39; EtOAC:hexanes) provided N-(4'-iodophenyl)-2-aminooctane (14.6 g, 88%) as a light yellow oil.

出典