Tetrahydrofuran → (4,5-Dicyclopropyl-2-isopropoxyphenyl)methanol

HRID 2272476Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2272476
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][CH:23]([CH3:25])[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][CH:23]([CH3:25])[CH3:24])[CH:10]=2)[CH2:7][CH2:8]1

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 90423073Methyl 4,5-dicyclopropyl-2-isopropoxybenzoate

Produkt 1

HCID 90423712(4,5-Dicyclopropyl-2-isopropoxyphenyl)methanolAusbeute 98,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A THF (15 mL) solution of methyl 4,5-dicyclopropyl-2-isopropoxybenzoate (5.90 g) was added at 0 C to a mixture of lithium aluminum hydride (1.71 g) and THF (85 mL), and the resultant mixture was stirred at room temperature for 30 minutes in a nitrogen atmosphere. Water (1.8 mL), a 1 M aqueous sodium hydroxide solution (1.8 mL), and water (5.4 mL) were added in this order to the reaction mixture at 0 C. The mixture was filtered through celite, and 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 (5.22 g).

Aufarbeitung

  1. filtrationThe mixture was filtered through celite
  2. concentrationthe 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-071f69b597384e4896b1d8dd062b9dd3
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120777B2

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