Reaktion #79568

Reaktionsgleichung

2-chloro-N-(1,3,3-trimethylbicyclo[2,2,1]hept-2-yl)acetamide

N-cyclohexylaniline

LiHMDS

Water

→

2-(cyclohexylphenylamino)-N-(1,3,3-trimethylbicyclo[2.2.1]hept-2-yl)acetamide

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigerecooled to −78° C.
2. 2
   Temperaturto warm to room temperature
3. 3
   Extraktionthe mixture was extracted with ethyl acetate
4. 4
   WaschenThe organic layer was washed with brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   SonstigeThe ethyl acetate solution was absorbed onto silica gel, which
7. 7
   Waschenwas eluted with 3% methanol/methylene chloride

Vorschrift

To a solution of N-cyclohexylaniline (100 mg, 0.56 mmol) in tetrahydrofuran (4 ml) at −78° C. was added LiHMDS (1 ml of a 1M solution in tetrahydrofuran) dropwise. The solution was allowed to warm to 0° C., then recooled to −78° C., and a solution of 2-chloro-N-(1,3,3-trimethylbicyclo[2,2,1]hept-2-yl)acetamide (124 mg, 0.56 mmol) in tetrahydrofuran (1 ml) added dropwise. The mixture was allowed to warm to room temperature, and was stirred for 1 hour. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate. The ethyl acetate solution was absorbed onto silica gel, which was eluted with 3% methanol/methylene chloride, to yield 2-(cyclohexylphenylamino)-N-(1,3,3-trimethylbicyclo[2.2.1]hept-2-yl)acetamide.

Quelle