Water → Cyclopentyl(3,5-dimethoxyphenyl)methanone

HRID 417054

Reaktionsgleichung

Reaktionsgleichung von HRID 417054
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[C:6]#N.[CH:13]1([Mg]Cl)[CH2:17][CH2:16][CH2:15][CH2:14]1.O.S(=O)(=O)(O)[OH:22]>C1COCC1.C(OCC)C>[CH:13]1([C:6]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=2)=[O:22])[CH2:17][CH2:16][CH2:15][CH2:14]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 294821-(Cyanomethyl)-3,5-dimethoxybenzeneHCID 178478989HCID 178478989, Verbindung

Produkt 1

HCID 11543194Cyclopentyl(3,5-dimethoxyphenyl)methanoneAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3,5-dimethoxybenzonitrile (5.0 g) in anhydrous THF (60 mL) were added a solution of cyclopentylmagnesium chloride (20 mL of 2 M solution in diethyl ether) and cuprous bromide (88 mg). The resulting reaction mixture was refluxed for 1 h. Then water (10 mL) and 10% sulfuric acid (20 mL) were added and the resulting mixture was stirred at room temperature overnight. Then the reaction mixture was diluted with diethyl ether and washed with water and brine. The organic extract was dried over anhydrous sodium sulfate, concentrated and purified on a silica gel column using ethyl acetate and hexanes to yield 5.9 of the title compound (82% yield). HRMS calcd for C14H18O3 [M+H]+ 253.1329, observed 253.1328.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 1 h
  3. washwashed with water and brine
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-834c853154724f7ab769e0844b4cdc2f
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088936B2

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