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

HRID 547041Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 547041
[H-].COCCO[Al+]OCCOC.[Na+].[H-].[CH2:15]([C:17]([C:28]1[CH:33]=[CH:32][C:31]([C:34]#[C:35][C:36]2([OH:42])[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[C:30]([CH3:43])[CH:29]=1)([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([CH3:27])[CH:21]=1)[CH2:18][CH3:19])[CH3:16]>O1CCCC1.[Cl-].[Na+].O.C(OCC)(=O)C>[CH2:15]([C:17]([C:28]1[CH:33]=[CH:32][C:31](/[CH:34]=[CH:35]/[C:36]2([OH:42])[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)=[C:30]([CH3:43])[CH:29]=1)([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([CH3:27])[CH:21]=1)[CH2:18][CH3:19])[CH3:16]

Komponenten

6

Edukt 2

HCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 577089754-{4-[1-Ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenylethynyl}-tetrahydro-pyran-4-ol

Produkt 1

HCID 574541474-((E)-2-{4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl}-vinyl)-tetrahydro-pyran-4-olAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium bis(2-methoxyethoxy)aluminum hydride (65 wt % solution in toluene, 1.06 mL, 3.516 mmol) was added to a solution of 4-{4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenylethynyl}-tetrahydro-pyran-4-ol (Example 130-(1); 0.46 g, 1.172 mmol) in tetrahydrofuran (5 mL) in a nitrogen atmosphere at 0° C., and the mixture was stirred at 0° C. for three hours. Then, ethyl acetate and brine were added to the reaction mixture, which was further diluted with ethyl acetate. Thereafter, celite was added and the mixture was stirred at room temperature for three hours. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 30:70, 40 minutes) to give the target compound as a colorless oil (0.46 g, 99%).

Aufarbeitung

  1. additionThereafter, celite was added
  2. stirringthe mixture was stirred at room temperature for three hours
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 30:70, 40 minutes)

Quellen und Nachweise

ORD-Eintrag
ord-0a2a822fddc44afe9a4c3b110eeebf20
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935688B2

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