Methyl iodide → 1-Methoxy-4-(1-phenyl-cyclohexyl)-benzene

HRID 70727

Reaktionsgleichung

Reaktionsgleichung von HRID 70727
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:22]I>CN(C=O)C>[CH3:22][O:19][C:16]1[CH:15]=[CH:14][C:13]([C:7]2([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15384544-(1-Phenylcyclohexyl)phenol

Produkt 1

HCID 116805591-Methoxy-4-(1-phenyl-cyclohexyl)-benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-(1-phenylcyclohexyl)phenol (20 mg, 0.08 mmol) was dissolved in DMF (2 mL). A suspension of NaH in oil (60%, 5 mg, 0.125 mmol) was added. After stirring for 5 minutes methyl iodide (0.05 mL; 0.8 mmol) was added. The reaction mixture was stirred for 2 h. (tic indicated full conversion of the starting material) then quenched with water (10 mL). Dichloromethane (10 mL) was added. The mixture was shaken and the organic phase separated off, dried (Na2SO4) and concentrated to syrup. The title product was afforded after work-up by flash-chromatography (eluent dichloromethane). Yield: 20 mg, quantitatively. LC-MS purity (UV/MS): 100/-, Rt 6.48 min. 1H NMR data were in accordance with the data written above.

Aufarbeitung

  1. additionwas added
  2. additionwas added
  3. customthen quenched with water (10 mL)
  4. additionDichloromethane (10 mL) was added
  5. stirringThe mixture was shaken
  6. customthe organic phase separated off
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated to syrup

Quellen und Nachweise

ORD-Eintrag
ord-d8eb85fccac34c548f9e8bd445fa85a3
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822548B2

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