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

반응식

[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

참가 물질

반응물 4

HCID 3283Diethyl Ether

HCID 24386Thionyl Chloride

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

HCID 178418306HCID 178418306, 화합물

생성물 1

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

반응 조건

온도: -78 °C

실험 절차

To a solution of 6-(2-methyl-1,3-dioxolan-2-yl)]-3,4-dihydro-4,4-dimethylnaphthlen-1(2H)-one ((Compound D1S, 353 mg, 1.36 mmol) in 3 ml of dry ether at −78° C. was added dropwise t-BuLi (1 ml, 1.7 mmol, 1.7 M solution in pentane). This clear light yellow solution was left at −78° C. for 30 min. Then, freshly 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.