Hydrochloric Acid → 6-[(2-Methylbut-3-yn-2-yl)oxy]quinoline

HRID 2425342Notes

Reaction equation

[CH3:1][C:2]([OH:6])([C:4]#[CH:5])[CH3:3].FC(F)(F)C(O)=O.O[C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2.Cl>C(#N)C.[Cu]Cl>[CH3:1][C:2]([O:6][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)([CH3:3])[C:4]#[CH:5]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-methyl-3-butyn-2-ol (2.45 mL, 25.1 mmol) and 1,8-diazabicyclo-[5.4.0]-7-undecene (4.25 mL, 28.4 mmol) in acetonitrile (15.5 mL) was stirred 0° C. for 30 minutes, and anhydrous trifluoroacetic acid (3.55 mL, 25.1 mmol) was added dropwise. The resulting mixture was added dropwise to a mixed solution of 6-hydroxyquinoline (2.43 g, 16.7 mmol), copper (I) chloride (8.3 mg, 0.0835 mmol), acetonitrile (15.5 mL) and 1,8-diazabicyclo-[5.4.0]-7-undecene (4.25 mL, 28.4 mmol) at 0° C., and stirred at 0° C. for 3 hours. The resulting solution was acidified with 1 mol/L HCl and extracted with ethyl acetate, and the resulting aqueous phase was neutralized with sodium hydrogencarbonate aqueous solution, extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by column chromatography (hexane/ethyl acetate=1/1 to 1/3) and the aimed product was obtained.

Workup

extractionextracted with ethyl acetate
extractionextracted with ethyl acetate
dry with materialdried over anhydrous magnesium sulfate
distillationAfter distilling off the solvent
customthe residue was purified by column chromatography (hexane/ethyl acetate=1/1 to 1/3)

Sources & evidence

ORD record: ord-1140ea18f858425baa2d397fb869d457
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964623B2

Reaction notes

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