3-Butyn-2-ol, 4-bromo-2-methyl- → 5-hydroxy-5-methyl-1-[3-(N-methylamino)phenyl] hexa-1,3-diyne

HRID 1614381

Reaction equation

HRID 1614381 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[NH:6][CH3:7])#[CH:2].Br[C:12]#[C:13][C:14]([OH:17])([CH3:16])[CH3:15]>C(N)(C)C.CO.[Cu]Cl>[OH:17][C:14]([CH3:16])([CH3:15])[C:13]#[C:12][C:2]#[C:1][C:3]1[CH:10]=[CH:9][CH:8]=[C:5]([NH:6][CH3:7])[CH:4]=1

Participants

6

Reactant 2

HCID 2004273-Butyn-2-ol, 4-bromo-2-methyl-HCID 197738093-ethynyl-N-methylaniline

Product 1

HCID 197738175-hydroxy-5-methyl-1-[3-(N-methylamino)phenyl] hexa-1,3-diyneYield 72.9%

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 887MethanolSolventHCID 6363IsopropylamineSolvent

Procedure

100 mg of copper (I) chloride were dissolved in a mixture of 20 ml of isopropylamine and 10 ml of methanol in an atmosphere of argon, and 1350 mg of 3-ethynyl-N-methylaniline were then added to the reaction mixture, followed by stirring at room temperature for 10 minutes. 3300 mg of 1-bromo-3-hydroxy-3-methyl-1-butyne were then dropwisely added to the solution over a time of about 3 hours, followed by stirring at room temperature for 2 hours. After the solvent had been evaporated from the reaction mixture, the residue was neutralized and diluted by 1N hydrochloric acid and subjected to extraction with 50 ml of ether three times. The organic layer was dried over magnesium sulfate, and the solvent was then evaporated. The residue was then purified by silica-gel chromatography using benzene as an eluent to obtain 1600 mg of 5-hydroxy-5-methyl-1-[3-(N-methylamino)phenyl] hexa-1,3-diyne.

Workup

  1. additionwere then added to the reaction mixture
  2. stirringby stirring at room temperature for 2 hours
  3. customAfter the solvent had been evaporated from the reaction mixture
  4. additiondiluted by 1N hydrochloric acid
  5. extractionsubjected to extraction with 50 ml of ether three times
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customthe solvent was then evaporated
  8. customThe residue was then purified by silica-gel chromatography

Sources & evidence

ORD record
ord-215e1af49e9c454d834c4837b45a4e8f
Source dataset
uspto-grants-1993_03
Patent number
US05196586

Linked notes

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