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

HRID 1388

Reaktionsgleichung

Reaktionsgleichung von HRID 1388
[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

Komponenten

5

Edukt 4

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 2365474,4-Dimethyl-3,4-dihydro-2H-naphthalen-1-oneHCID 178418306HCID 178418306, Verbindung

Produkt 1

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

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-130b3a00a9dc43f5a473799157e45ada
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723666

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