Reaktion #1484

Reaktionsgleichung

SOCl2

3,4-dihydro-4,4-dimethylnaphthlen-1(2H)-one

t-BuLi

ether

→

title compound

3,4-Dihydro-4,4-dimethyl-6-acetyl-1-(1,1-dimethylethyl)naphthalene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturslowly warmed to room temperature
2. 2
   SonstigeThe reaction was quenched by addition of saturated NH4Cl
3. 3
   SonstigeThe white solids were removed by filtration
4. 4
   Einengenthe clear solution was concentrated to an oil
5. 5
   Sonstigepurified by column chromatography with ethyl acetate/hexane (1/10)

Vorschrift

To a solution of 6-(2-methyl-1,3-dioxolan-2-yl)!-3,4-dihydro-4,4-dimethylnaphthlen-1(2H)-one ((Compound D15, 353 mg, 1.36 mmol) in 3 ml of dry ether at -78° C. was added dropwise t-BuLi (1 ml, 1.7 mmol, 1.7M solution in pentane). This dear light yellow solution was left at -78° C. for 30 min. Then, fleshly distilled SOCl2 (0.15 ml, 2.0 mmol) was added. The reaction mixture was stirred at -78° C. for additional 30 min and thereafter slowly warmed to room temperature. The reaction was quenched by addition of saturated NH4Cl. The white solids were removed by filtration and the clear solution was concentrated to an oil, and purified by column chromatography with ethyl acetate/hexane (1/10) to give the title compound as a yellow oil.

Quelle