3-Butyn-2-ol, 4-bromo-2-methyl- → 5-Hydroxy-5-methyl-1-(4-methoxyphenyl)hexa-1,3-diyne

HRID 1614375

Reaktionsgleichung

Reaktionsgleichung von HRID 1614375
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1)#[CH:2].Br[C:12]#[C:13][C:14]([OH:17])([CH3:16])[CH3:15].Cl.NO>C(N)(C)C.CO.[Cu]Cl.[Cu+2]>[OH:17][C:14]([CH3:16])([CH3:15])[C:13]#[C:12][C:2]#[C:1][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1

Komponenten

8

Edukt 3

HCID 2004273-Butyn-2-ol, 4-bromo-2-methyl-HCID 2510201-Ethynyl-4-methoxybenzeneHCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 197738155-Hydroxy-5-methyl-1-(4-methoxyphenyl)hexa-1,3-diyneAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 27099Cupric cationKatalysator2×HCID 62652Cuprous chlorideKatalysatorHCID 887MethanolLösungsmittelHCID 6363IsopropylamineLösungsmittel

Versuchsvorschrift

100 mg of copper (I) chloride was dissolved in a mixture of 20 ml of isopropylamine and 20 ml of methanol in an atmoshpere of argon, and 1320 mg of 4-ethynylanisole were added to the resultant solution, followed by stirring at room temperature for 10 minutes. 2700 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 fo 2 hours (If the solution is colored green owing to the production of copper (II) ion, an appropriate amount of hydroxilamine hydrochloride is added so as to reduce the copper (II) ion). The solvent was then evaporated from the reaction mixture, and the residue was neutralized and diluted by 1N hydrochloric acid, and then subjected to extraction with 50 ml of dichloromethane three times. The organic layer was 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 1500 mg of 5-hydroxy-5-methyl-1-(4-methoxyphenyl)hexa-1,3-diyne.

Aufarbeitung

  1. stirringby stirring at room temperature
  2. waitfo 2 hours
  3. customThe solvent was then evaporated from the reaction mixture
  4. additiondiluted by 1N hydrochloric acid
  5. extractionsubjected to extraction with 50 ml of dichloromethane 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 column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4350b3fd29c94dcaa1f8276f7708ba9c
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05196586

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