Water → HCID 12598593, Verbindung

HRID 1071615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1071615
[CH3:1][CH:2]([CH3:10])[CH2:3][CH2:4][C:5]([O:7]CC)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1[CH2:21][CH2:20][CH2:19][CH2:18]1.O.[OH-].[Na+].O1CC[CH2:27][CH2:26]1>C(OCC)C>[CH3:10][CH:2]([CH3:1])[CH:3]([C:18]1[CH:27]=[CH:26][CH:21]=[CH:20][CH:19]=1)[CH2:4][CH2:5][OH:7]

Komponenten

7

Edukt 5

HCID 962Water2×HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 117477Ethyl 4-methylpentanoateHCID 68718528lithium aluminium hydride THF

Produkt 1

HCID 12598593HCID 12598593, VerbindungAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, ethyl 4-methylpentanoate (350 mg) was dissolved in tetrahydrofuran (10 mL) at −78° C., a lithium aluminum hydride/tetrahydrofuran solution (1.0 M, 1.58 mL) was added, and the mixture was stirred. While the temperature of the mixture was naturally returned to room temperature, the mixture was stirred, and after 1.5 hours, water (0.05 mL), a 2N aqueous sodium hydroxide (0.05 mL) and water (0.15 mL) were successively added thereto, and the mixture was stirred. Further, diethyl ether was added thereto, and then the resulting insoluble matters were filtered off and the filtrate was evaporated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate system), to give the title compound as a colorless oil (257 mg, 42%: 2 steps).

Aufarbeitung

  1. customwas naturally returned to room temperature
  2. stirringthe mixture was stirred
  3. stirringthe mixture was stirred
  4. filtrationthe resulting insoluble matters were filtered off
  5. customthe filtrate was evaporated
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-cb47566cf49245fb83e68747abce4840
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06906072B1

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