Sodium bis(2-methoxyethoxy)aluminiumhydride → 4-(1-ethyl-1-{4-[(E)-2-(1-hydroxy-cyclopentyl)-vinyl]-3-methyl-phenyl}-propyl)-2-methyl-phenol

HRID 546861Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 546861
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[CH2:15]([C:17]([C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[C:37]([CH3:42])[CH:36]=1)([C:20]1[CH:25]=[CH:24][C:23]([C:26]#[C:27][C:28]2([OH:33])[CH2:32][CH2:31][CH2:30][CH2:29]2)=[C:22]([CH3:34])[CH:21]=1)[CH2:18][CH3:19])[CH3:16]>O1CCCC1.C(OCC)(=O)C.[Cl-].[Na+].O>[CH2:15]([C:17]([C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[C:37]([CH3:42])[CH:36]=1)([C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]2([OH:33])[CH2:32][CH2:31][CH2:30][CH2:29]2)=[C:22]([CH3:34])[CH:21]=1)[CH2:18][CH3:19])[CH3:16]

Komponenten

6

Edukt 2

HCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 574833964-{1-Ethyl-1-[4-(1-hydroxy-cyclopentylethynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenol

Produkt 1

HCID 574629914-(1-ethyl-1-{4-[(E)-2-(1-hydroxy-cyclopentyl)-vinyl]-3-methyl-phenyl}-propyl)-2-methyl-phenolAusbeute 92,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Sodium bis(2-methoxyethoxy)aluminum hydride (3.33 M solution in toluene, 6.7 mL, 22.3 mmol) was added to a solution of 4-{1-ethyl-1-[4-(1-hydroxy-cyclopentylethynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenol (Example 32-(1); 2.8 g, 7.4 mmol) in tetrahydrofuran (37 mL) at 0° C., and the mixture was stirred at the same temperature for four hours. The reaction mixture was diluted with ethyl acetate. Brine and celite were added, and the mixture was stirred at room temperature for 30 minutes. The organic layer was dried over anhydrous magnesium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane only to hexane/ethyl acetate=3/1) to give the title compound (2.6 g, 92%).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (hexane only to hexane/ethyl acetate=3/1)

Quellen und Nachweise

ORD-Eintrag
ord-fd746b5cda4d43c49a8e37d9f6c5d7c9
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935688B2

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