3-Methylbutanal → 3-Methyl-1-(pyrazin-2-yl)butan-1-ol

HRID 1046575Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1046575
I[C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.[Li]CCCC.[CH:13](=[O:18])[CH2:14][CH:15]([CH3:17])[CH3:16].[NH4+].[Cl-]>C(OCC)C>[CH3:16][CH:15]([CH3:17])[CH2:14][CH:13]([C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1)[OH:18]

Komponenten

6

Edukt 4

HCID 115523-MethylbutanalHCID 25517Ammonium ChlorideHCID 642841IodopyrazineHCID 178418339Butyllithium

Produkt 1

HCID 607985673-Methyl-1-(pyrazin-2-yl)butan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 2-iodopyrazine (10.0 g, 48.5 mmol) in diethyl ether at −50° C. was added dropwise n-BuLi (2.5 M in hexanes, 25 mL, 60.7 mmol), immediately followed by addition of isovaleraldehyde (8.13 mL, 6.48 g, 75 mmol) over 5 minutes. The mixture was allowed to reach room temperature and was added to a saturated NH4Cl solution. The aqueous phase was extracted with TBME (3×100 mL) and the combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. The resulting oil was filtered over a plug of silica to afford 3-methyl-1-(pyrazin-2-yl)butan-1-ol as a yellow-brownish oil (5.5 g; 68%).

Aufarbeitung

  1. customto reach room temperature
  2. extractionThe aqueous phase was extracted with TBME (3×100 mL)
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. filtrationThe resulting oil was filtered over a plug of silica

Quellen und Nachweise

ORD-Eintrag
ord-593b9a91784a4c7cac5fad539deb954d
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569337B2

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