Cerium(III) chloride → Methyl 4-(4-hydroxy-4-methylcyclohex-1-en-1-yl)benzoate

HRID 2356125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2356125
[Cl-].[Ce+3].[Cl-].[Cl-].[CH3:5][Li].[Cl-].[Li+].[O:9]=[C:10]1[CH2:15][CH2:14][C:13]([C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)=[CH:12][CH2:11]1>C1COCC1.C(OCC)C.C(OCC)(=O)C>[OH:9][C:10]1([CH3:5])[CH2:15][CH2:14][C:13]([C:16]2[CH:17]=[CH:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:24][CH:25]=2)=[CH:12][CH2:11]1

Komponenten

8

Edukt 4

HCID 24636Cerium(III) chlorideHCID 433294Lithium ChlorideHCID 22730167Methyl 4-(4-oxocyclohex-1-en-1-yl)benzoateHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 22730725Methyl 4-(4-hydroxy-4-methylcyclohex-1-en-1-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of anhydrous cerium(III) chloride (2.71 g, 11 mmol) in THF (10 mL) at −78° C. was slowly treated with 1.5M methyllithium complexed with lithium chloride in diethyl ether (6.7 mL), warmed to room temperature over 2 hours, and added to a solution of Example 420C (1.15 g, 5.0 mmol) in THF (10 mL) at −78° C. The reaction was gradually warmed to room temperature over 4 hours, diluted with ethyl acetate (100 mL), washed with water (45 mL) and brine (10 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 10-30% ethyl acetate/hexanes to provide the desired product.

Aufarbeitung

  1. temperatureThe reaction was gradually warmed to room temperature over 4 hours
  2. washwashed with water (45 mL) and brine (10 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography on silica gel with 10-30% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-dab765b87b664b5d826a57568fdc2afc
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07754886B2

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