Water → {2-(2,3,4,5-Tetramethylcyclopentadienyl)phenyl}phenylmethylalcohol

HRID 15698

Reaktionsgleichung

Reaktionsgleichung von HRID 15698
[CH3:1][C:2]1[CH:3]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]=[O:13])[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7].[C:18]1([Li])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O.C1(C)C=CC=CC=1>O1CCCC1.C1CCCCC1.CCOCC>[CH3:1][C:2]1[CH:3]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[CH:12]([OH:13])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7]

Komponenten

8

Edukt 4

HCID 962WaterHCID 1140TolueneHCID 1317271152-(2,3,4,5-Tetramethylcyclopentadienyl)benzaldehydeHCID 178506676HCID 178506676, Verbindung

Produkt 1

HCID 131727116{2-(2,3,4,5-Tetramethylcyclopentadienyl)phenyl}phenylmethylalcoholAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(2,3,4,5-tetramethylcyclopentadienyl)benzaldehyde (2.0 g, 8.80 mmol) in tetrahydrofuran (34.0 mL) was added dropwise a 1.05 M solution of phenyllithium in cyclohexane and ether (17.7 mL) at −78° C. The temperature of the mixture was raised to room temperature and the mixture was stirred for 4 hrs. To the reaction mixture solution were added deionized water (20.0 mL) and toluene (20.0 mL) to separate an organic layer and an aqueous layer. The organic layer was dried over sodium sulfate, then distilled to remove the solvent, and purified by a silica gel column (hexane/ethyl acetate=9/1) to give {2-(2,3,4,5-tetramethylcyclopentadienyl)phenyl}phenylmethylalcohol (2.83 g, yield 87.0%) as a pale yellow oily substance.

Aufarbeitung

  1. customto separate an organic layer
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. distillationdistilled
  4. customto remove the solvent
  5. custompurified by a silica gel column (hexane/ethyl acetate=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-26e9f2d2099144b3b3ab23636d67b9e4
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732643B2

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