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Sodium Iodide → HCID 58622877, Verbindung

HRID 1269654
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1269654
Cl[CH2:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH3:16])[CH:4]=1.[I-].[Na+].[CH2:19]([NH:23][C:24]1[C:25]([CH3:37])=[C:26]([C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)[CH:27]=[CH:28][CH:29]=1)[CH2:20][CH2:21][CH3:22]>C(#N)C>[CH2:19]([N:23]([CH2:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH3:16])[CH:4]=1)[C:24]1[C:25]([CH3:37])=[C:26]([C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)[CH:27]=[CH:28][CH:29]=1)[CH2:20][CH2:21][CH3:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 5238Sodium IodideHCID 16109205HCID 16109205, VerbindungHCID 18448422HCID 18448422, Verbindung

Produkt 1

HCID 58622877HCID 58622877, VerbindungAusbeute 78,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

Ethyl [4-(chloromethyl)-2-methylphenoxy]acetate (35.9 g, 0.148 mols) was dissolved in dry acetonitrile (285 mL). Sodium iodide (20.1 g, 0.135 mols 1 eq) was added in one portion and mixture stirred for 5 mins. A solution of the N-butyl-N-(2,4′-dimethyl-1,1′-biphenyl-3-yl)amine (34 g. 0.135 mol) and disopropylethylamine (23.5 mL, 0.135 mol) in dry acetonitrile (285 mL) was added over 10 min and cooling applied to maintain reaction temperature at ca. 16° C. during the addition. The reaction was concentrated in vacuo and the resultant orange oil partitioned between DCM (700 mL) and water (700 mL). The aqueous was extracted with DCM (500 mL) and the combined organic extracts were cautiously washed with brine (300 mL). After drying (Na2SO4) the mixture was concentrated in vacuo to give a dark orange oil. Purification using flash chromatography on (2 kg silica column), eluting with 1:1–0:1 cyclohexane:DCM afforded the title compound as a yellow oil (48.8 g).

Aufarbeitung

  1. temperaturecooling
  2. temperatureto maintain
  3. customreaction temperature at ca. 16° C.
  4. additionduring the addition
  5. concentrationThe reaction was concentrated in vacuo
  6. customthe resultant orange oil partitioned between DCM (700 mL) and water (700 mL)
  7. extractionThe aqueous was extracted with DCM (500 mL)
  8. washthe combined organic extracts were cautiously washed with brine (300 mL)
  9. dry with materialAfter drying (Na2SO4) the mixture
  10. concentrationwas concentrated in vacuo
  11. customto give a dark orange oil
  12. customPurification
  13. washeluting with 1:1–0:1 cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-10b7a9e7dc0b4cda912d2c73e9aee2db
Quelldatensatz
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07199239B2

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