2-Methylpyridine → 2,4-Dimethyl-3-pyridin-2-ylmethyl-pentan-3-ol

HRID 447092

Reaktionsgleichung

Reaktionsgleichung von HRID 447092
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])(C)(C)C.[CH3:13][CH:14]([C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])[CH3:15]>C1COCC1>[CH3:13][CH:14]([C:16]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)([OH:20])[CH:17]([CH3:19])[CH3:18])[CH3:15]

Komponenten

5

Edukt 3

HCID 79752-MethylpyridineHCID 112712,4-Dimethyl-3-pentanoneHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 161262742,4-Dimethyl-3-pyridin-2-ylmethyl-pentan-3-olAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

2-Methyl-pyridine (1.86 g, 20 mmol) is dissolved in THF (20 mL) and cooled to −30° C. tert-Butyl lithium (11.8 mL, 1.7M in pentane, 20 mmol) is added dropwise to the solution, and the reaction is stirred for 30 min at −30° C. 2,4-Dimethyl-pentan-3-one (3.4 mL, 24 mmol) is added and the reaction is warmed to room temperature and stirred for 2 h. Add H2O (30 mL) and extract with EtOAc. Wash combined organics with brine and concentrate in vacuo. The residue is purified by flash chromatography on silica gel (EtOAc/Heptane) to afford 2,4-dimethyl-3-pyridin-2-ylmethyl-pentan-3-ol (4.14 g, quant.).

Aufarbeitung

  1. additionis added dropwise to the solution
  2. temperaturethe reaction is warmed to room temperature
  3. stirringstirred for 2 h
  4. extractionAdd H2O (30 mL) and extract with EtOAc
  5. washWash
  6. concentrationconcentrate in vacuo
  7. customThe residue is purified by flash chromatography on silica gel (EtOAc/Heptane)

Quellen und Nachweise

ORD-Eintrag
ord-afa77a35db864366800576026aaa111f
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481542B2

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