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

Temperature

0 °C

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.

1. temperatureThe mixture was refluxed
2. temperatureThe mixture was refluxed for one hour after which it
3. additionwere added
4. stirringthe mixture was stirred overnight at room temperature
5. extractionThe mixture was extracted with methylene chloride
6. dry with materialdried over sodium sulfate
7. customevaporated

ORD record

ord-d34262a676634d269babbf51150d3970

Source dataset

uspto-grants-1995_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05426226