Reaktion #50412

Reaktionsgleichung

3-bromofuran

3-bromofuran

ammonium hydroxide

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

magnesium

→

residue

Ausbeute 84.1%

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

Ausbeute 84.1%

Lösungsmittel

toluene

water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was refluxed
2. 2
   TemperaturThe 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
   ExtraktionThe mixture was extracted with methylene chloride
6. 6
   Trocknendried over sodium sulfate
7. 7
   Sonstigeevaporated

Vorschrift

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.

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