3-Butyn-2-ol, 4-bromo-2-methyl- → 6-(3-Methoxyphenyl)-2-methylhexa-3,5-diyn-2-ol

HRID 1614378

반응식

HRID 1614378 반응식
[C:1]([C:3]1[CH:4]=[C:5]([O:9][CH3:10])[CH:6]=[CH:7][CH:8]=1)#[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:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1

참가 물질

6

반응물 2

HCID 2004273-Butyn-2-ol, 4-bromo-2-methyl-HCID 6407531-Ethynyl-3-methoxybenzene

생성물 1

HCID 197738166-(3-Methoxyphenyl)-2-methylhexa-3,5-diyn-2-ol수율 74.8%

시약·촉매·용매 3

HCID 62652Cuprous chloride촉매HCID 887Methanol용매HCID 6363Isopropylamine용매

실험 절차

50 mg of copper (I) chloride were dissolved in a mixture of 10 ml of isopropylamine and 15 ml of methanol in an atmosphere of argon, and 660 mg of 3-ethynylanisole were then added to the reaction mixture, followed by stirring at room temperature for 10 minutes. 1300 mg of 1-bromo-3-hydroxy-3-methyl-1-butyne were then dropwisely added to the solution over a time of about 2 hours, followed by stirring at room temperature for 2 hours. The solvent was then evaporated from the reaction mixture, and the residue was then neutralized and diluted by 1N hydrochloric acid, and subjected to extraction with dichloromethane three times. The organic layer was then dried over magnesium sulfate, and the solvent was then evaporated. The residue was then purified by silica-gel column chromatography using benzene as an eluent to obtain 800 mg of 5-hydroxy-5-methyl-1-(3-methoxyphenyl)hexane-1,3-diyne.

후처리

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

출처 및 근거

ORD 기록
ord-51193511cf39407e9d77f2d00dc4bdb4
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05196586

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