Reaktion #90169

Reaktionsgleichung

X-phos

trimethylsilylacetylene

6-Bromo-7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one

→

title compound

6-Ethynyl-7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one

Lösungsmittel

ethyl acetate

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe organic layer was washed twice with 10% brine
2. 2
   Einengenconcentrated under reduced pressure
3. 3
   workup.DISSOLUTIONThe resulting residues were dissolved in THF (10 ml)
4. 4
   workup.ADDITIONadded with the THF solution (4 ml)
5. 5
   workup.STIRRINGstirred at room temperature for 1 hr
6. 6
   workup.ADDITIONThe reaction mixture was diluted with ethyl acetate (100 ml)
7. 7
   WaschenThe organic layer was washed twice with 10% brine
8. 8
   Einengenconcentrated under reduced pressure
9. 9
   SonstigeThe resulting residues were purified by silica gel column (n-hexane/ethyl acetate=9/1)

Vorschrift

6-Bromo-7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (1 g) was dissolved in acetonitrile (50 ml), added with PdCl2(CH3CN)2 (45 mg), X-phos (168 mg), CsCO3 (1.2 g) and trimethylsilylacetylene (0.9 ml), and the mixture was stirred at 85° C. for 2 hrs. The reaction mixture was diluted with ethyl acetate (100 ml). The organic layer was washed twice with 10% brine and concentrated under reduced pressure. The resulting residues were dissolved in THF (10 ml), added with the THF solution (4 ml) comprising tetrabutylammonium fluoride and stirred at room temperature for 1 hr. The reaction mixture was diluted with ethyl acetate (100 ml). The organic layer was washed twice with 10% brine and concentrated under reduced pressure. The resulting residues were purified by silica gel column (n-hexane/ethyl acetate=9/1) to obtain the title compound (346 mg, two step yield 43%).

Quelle