Diethyl Ether → 3,4-Dihydro-4,4-dimethyl-6-acetyl-1-(1,1-dimethlethyl)naphthalene

反応式

[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=O)[CH2:4][CH2:3]1.[Li][C:15]([CH3:18])([CH3:17])[CH3:16].O=S(Cl)Cl.[CH3:23][CH2:24][O:25]CC>>[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:24](=[O:25])[CH3:23])[CH:10]=2)[C:5]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH2:3]1

参加物

反応物 4

HCID 3283Diethyl Ether

HCID 24386Thionyl Chloride

HCID 2365474,4-Dimethyl-3,4-dihydro-2H-naphthalen-1-one

HCID 178418306HCID 178418306、化合物

生成物 1

HCID 225715533,4-Dihydro-4,4-dimethyl-6-acetyl-1-(1,1-dimethlethyl)naphthalene

反応条件

温度: -78 °C

実験手順

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.