Imidazole → 4-Phenylcyclohexylmethyl iodide

HRID 2269348

Reaktionsgleichung

Reaktionsgleichung von HRID 2269348
N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:25]I.[C:27]1([CH:33]2[CH2:38][CH2:37][CH:36]([CH2:39]O)[CH2:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>ClCCl.CCCCC>[C:27]1([CH:33]2[CH2:38][CH2:37][CH:36]([CH2:39][I:25])[CH2:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 3100608(4-Phenylcyclohexyl)methanol

Produkt 1

HCID 183339764-Phenylcyclohexylmethyl iodideAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8003PentaneLösungsmittel

Versuchsvorschrift

Imidazole (4.4 g, 0.065 mol) is added in one portion to a solution of triphenylphosphine (17.0 g, 0.065 mol) in dichloromethane (300 mL) at 25° C. After all of the solids dissolved, iodine (16.5 g, 0.065 mol) is added in four portions. The mixture is stirred for 10 min. then a solution of 4-phenylcyclohexylmethanol (10.5 g, 0.055 mol) is added dropwise and the mixture is stirred at 25° C. for 18 h. The reaction mixture is poured into pentane and the resulting solids filtered. The filtrate is concentrated in vacuo and the residue is dissolved in dichloromethane. This solution is poured into hexanes, the solids were filtered, and the filtrate is concentrated in vacuo. The residue is passed through a pad of silica gel using hexanes as eluent to afford 14.6 g (89%) of 4-phenylcyclohexylmethyl iodide as an oil.

Aufarbeitung

  1. dissolutionAfter all of the solids dissolved
  2. stirringthe mixture is stirred at 25° C. for 18 h
  3. filtrationthe resulting solids filtered
  4. concentrationThe filtrate is concentrated in vacuo
  5. dissolutionthe residue is dissolved in dichloromethane
  6. additionThis solution is poured into hexanes
  7. filtrationthe solids were filtered
  8. concentrationthe filtrate is concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-41eb19a3db80431290c4337f10d21054
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06329400B1

Verknüpfte Notizen

Wird geladen…