Реакция #1484

Уравнение реакции

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

Условия реакции

Обработка

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

Методика

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.

Источник