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

HRID 1614381

반응식

HRID 1614381 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 62652Cuprous chloride촉매HCID 887Methanol용매HCID 6363Isopropylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-215e1af49e9c454d834c4837b45a4e8f
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05196586

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