Iodine → 1-Quinoxalin-2-yl-but-3-yn-1-ol

HRID 334694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 334694
[Mg].II.[CH2:4](Br)[C:5]#[CH:6].[N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][C:9]=1[CH:18]=[O:19].[NH4+].[Cl-]>CCOCC.C1COCC1>[N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][C:9]=1[CH:18]([OH:19])[CH2:6][C:5]#[CH:4]

Komponenten

8

Edukt 5

HCID 807IodineHCID 7842Propargyl bromideHCID 25517Ammonium ChlorideHCID 594088Quinoxaline-2-carbaldehydeHCID 5462224Magnesium

Produkt 1

HCID 866302471-Quinoxalin-2-yl-but-3-yn-1-olAusbeute 14,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of magnesium (229 mg, 9.41 mmol), mercuric chloride (13 mg, 47 μmol) and few crystals of iodine in Et2O (1.5 mL), a solution of propargyl bromide (0.53 mL, 5.88 mmol) in Et2O (4.5 mL) was added slowly in order to maintain a reflux. The reaction mixture was stirred 1 hour and added to a solution of quinoxaline-2-carbaldehyde (500 mg, 3.16 mmol) in THF (2 mL). The resulting reaction mixture was stirred at 0° C. for 30 min., at room temperature for 30 min. and was poured onto saturated NH4Cl solution. The aqueous phase was extracted with Et2O. The aqueous phase was washed with water, brine, dried over MgSO4, filtered and evaporated. The crude residue was purified by C18 flash chromatography (H2O/acetonitrile 100:0 to 80:20) to yield 90 mg (0.45 mmol, 14%) of 1-quinoxalin-2-yl-but-3-yn-1-ol as a yellow oil.

Aufarbeitung

  1. temperatureto maintain a reflux
  2. customThe resulting reaction mixture
  3. stirringwas stirred at 0° C. for 30 min., at room temperature for 30 min.
  4. extractionThe aqueous phase was extracted with Et2O
  5. washThe aqueous phase was washed with water, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude residue was purified by C18 flash chromatography (H2O/acetonitrile 100:0 to 80:20)

Quellen und Nachweise

ORD-Eintrag
ord-0f3a9936008745609b7dd2a151345d65
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883826B2

Notizen zur Reaktion

Wird geladen…