Reacción #6831

Ecuación de reacción

2,6,6-trimethoxy-6,7,8,9-tetrahydro-5H-benzocycloheptene

p-toluenesulfonic acid monohydrate

acetone

→

2-methoxy-5,7,8,9-tetrahydro-benzocyclohepten-6-one

Rendimiento 80.2%

Disolventes

water

dichloromethane

sodium hydrogen carbonate

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe aqueous layer was re-extracted with 50 mL more dichloromethane
2. 2
   Secadothe combined organics were dried over sodium sulfate
3. 3
   OtroEvaporation of the solvent

Procedimiento

A solution of 2,6,6-trimethoxy-6,7,8,9-tetrahydro-5H-benzocycloheptene (387 mg) and p-toluenesulfonic acid monohydrate (31 mg) was stirred in 5 mL of 1:1 water:acetone. The mixture was diluted with 50 mL of dichloromethane and 50 mL of saturated sodium hydrogen carbonate. The aqueous layer was re-extracted with 50 mL more dichloromethane and the combined organics were dried over sodium sulfate. Evaporation of the solvent gave 250 mg of 2-methoxy-5,7,8,9-tetrahydro-benzocyclohepten-6-one, which was converted to 2-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ylamine by using Procedure X.

Fuente