Water → 3-Pyridinepropanol

HRID 22487

Reaktionsgleichung

Reaktionsgleichung von HRID 22487
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9](/[CH:13]=[CH:14]/[C:15](OC)=[O:16])[CH:8]=1.O.[OH-].[Na+]>C(OCC)C>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH2:14][CH2:15][OH:16])[CH:8]=1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 53576873-Pyridineacrylic acid, methyl esterHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 178613-Pyridinepropanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To an ice cold mixture of lithium aluminium hydride (28 mg, 0.74 mmol) in dry diethyl ether (20 ml) was added dropwise methyl E-3-(3-pyridyl)acrylate (100 mg, 0.61 mmol) under argon. The resulting mixture was allowed to warm up to room temperature and stirred for 12 h. Water (0.1 ml), 15% aqueous sodium hydroxide (0.1 ml) and water (0.3 ml) were added sequentially over 0.5 h and the mixture allowed to stir for 1 h. The resulting suspension was filtered and the filtrate concentrated under reduced pressure. Flash chromatography (flash silica gel; 10% methanol in ethyl acetate) gave 3-(3-pyridyl)-1-propanol, which was discarded, and E-3-(3-pyridyl)-1-prop-2-enol (55 mg, 67%) as a colourless oil.

Aufarbeitung

  1. stirringto stir for 1 h
  2. filtrationThe resulting suspension was filtered
  3. concentrationthe filtrate concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-542be1b40c894345ad8add272bc4e44e
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428168

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