반응 #50412

반응 방정식

3-bromofuran

3-bromofuran

ammonium hydroxide

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

magnesium

→

residue

수율 84.1%

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

수율 84.1%

용매

toluene

water

THF

반응 조건

후처리

1. 1
   온도The mixture was refluxed
2. 2
   온도The 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
   추출The mixture was extracted with methylene chloride
6. 6
   건조dried over sodium sulfate
7. 7
   기타evaporated

실험 절차

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.

출처