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

HRID 1599890Notes

Reaction equation

HRID 1599890 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

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

Conditions

Temperature
-78 °C

Procedure

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 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.

Workup

  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)

Sources & evidence

ORD record
ord-c166d2a2544046a09b71df849f0893d6
Source dataset
uspto-grants-1998_04
Patent number
US05741896

Reaction notes

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