Reaktion #568381

Reaktionsgleichung

3,4-dihydro-4,4-dimethyl-7-bromo-naphthalen-1(2H)-one

7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1-one

Compound G

7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1-one

ethyl 4-vinylbenzoate

tris(2-methylphenyl) phosphine

→

title compound

Ethyl (E)-4-[2-(5,6-Dihydro-5,5-dimethyl-naphthalen-8(7H)-one-2-yl)ethenyl]-benzoate

Lösungsmittel

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to room temperature
2. 2
   Einengenconcentrated under reduced pressure
3. 3
   SonstigePurification by column chromatography (10% EtOAc/hexanes)

Vorschrift

To a solution of 520.0 mg (2.00 mmol) of 3,4-dihydro-4,4-dimethyl-7-bromo-naphthalen-1(2H)-one (Compound G), and 510.0 mg (2.90 mmol) of ethyl 4-vinylbenzoate in 4.0 mL of triethylamine (degassed by sparging with argon for 25 minutes), was added 124.0 mg (0.40 mmol) of tris(2-methylphenyl) phosphine, followed by 44.0 mg (0.20 mmol) of palladium(II)acetate. The resulting solution was heated to 95° C. for 2.5 h, cooled to room temperature, and concentrated under reduced pressure. Purification by column chromatography (10% EtOAc/hexanes) afforded the title compound as a colorless solid.

Quelle