Reacción #50412

Ecuación de reacción

3-bromofuran

3-bromofuran

ammonium hydroxide

2-Di-n-propylamino-8-bromo-1,2,3,4-tetrahydronaphthalene

magnesium

→

residue

Rendimiento 84.1%

2-Di-n-propylamino-8-(fur-3-yl)-1,2,3,4-tetrahydronaphthalene

Rendimiento 84.1%

Disolventes

toluene

water

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was refluxed
2. 2
   TemperaturaThe mixture was refluxed for one hour after which it
3. 3
   workup.ADDITIONwere added
4. 4
   workup.STIRRINGthe mixture was stirred overnight at room temperature
5. 5
   ExtracciónThe mixture was extracted with methylene chloride
6. 6
   Secadodried over sodium sulfate
7. 7
   Otroevaporated

Procedimiento

2-Di-n-propylamino-8-bromo-1,2,3,4-tetrahydronaphthalene (1.0 g; 3.2 mmol) was dissolved in 20 ml of THF, and 94 mg (3.9 mmol) of magnesium shavings were added. The mixture was refluxed, and a couple of drops of dibromoethane were added to initiate Grignard formation. The mixture was refluxed for one hour after which it was added to a solution of 0.58 ml (6.4 mmol) of 3-bromofuran and 36 mg (0.03 mmol) of Ni(PPh3)4 in 20 ml of toluene that had been cooled to 0° C. after stirring at room temperature for one hour. The mixture was stirred at room temperature for three hours after which an additional 0.58 ml of 3-bromofuran and 35 mg of Ni(PPh3)4 were added. When the reaction failed to proceed further, 210 mg (0.3 mmol) Ni(PPh3)2Cl2 was added, and the mixture was stirred overnight at room temperature. The mixture then was poured into water and the pH adjusted to 10 with ammonium hydroxide. The mixture was extracted with methylene chloride, dried over sodium sulfate, and evaporated to give 0.8 g of a residue.

Fuente