Tetrahydrofuran → 4,5-Dicyclopropyl-2-ethoxybenzenemethanol

HRID 531054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 531054
C1COCC1.[CH:6]1([C:9]2[C:18]([CH:19]3[CH2:21][CH2:20]3)=[CH:17][C:12]([C:13](OC)=[O:14])=[C:11]([O:22][CH2:23][CH3:24])[CH:10]=2)[CH2:8][CH2:7]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[CH:6]1([C:9]2[C:18]([CH:19]3[CH2:21][CH2:20]3)=[CH:17][C:12]([CH2:13][OH:14])=[C:11]([O:22][CH2:23][CH3:24])[CH:10]=2)[CH2:7][CH2:8]1

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 90423797Methyl 4,5-dicyclopropyl-2-ethoxybenzoate

Produkt 1

HCID 904239324,5-Dicyclopropyl-2-ethoxybenzenemethanolAusbeute 97,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A THF (15 mL) solution of methyl 4,5-dicyclopropyl-2-ethoxybenzoate (3.26 g) was added at 0° C. to a mixture of lithium aluminum hydride (1.09 g) and THF (65 mL), and the resultant mixture was stirred at room temperature for 1 hour in a nitrogen atmosphere. Water (1 mL), a 1 M aqueous sodium hydroxide solution (1 mL), and water (3 mL) were added in this order to the reaction mixture at 0° C., and the mixture was filtered through celite. Then, the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to obtain the title compound (2.84 g).

Aufarbeitung

  1. filtrationthe mixture was filtered through celite
  2. concentrationThen, the filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-5ec82e1b01784cc8ab4f28c7b3cf4312
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353108B2

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