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Hydrochloric Acid → 2-(4'-Methoxyphenyl)-5-octyloxypyridine

HRID 1768883
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1768883
Cl.[CH2:2]([O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([NH2:17])=N)=[CH:13][CH:12]=1)CCCCCCC.[CH2:20]([O:28][C:29]1[CH:34]=CC(C#N)=[CH:31][CH:30]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(=O)([O-])[O-].[Na+].[Na+].Cl>C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].C1(C)C=CC=CC=1>[CH3:2][O:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]2[CH:31]=[CH:30][C:29]([O:28][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:34][N:17]=2)=[CH:18][CH:19]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 1451614-(Octyloxy)benzonitrileHCID 122385044-n-Octyloxybenzamidine hydrochloride

Produkt 1

HCID 200979682-(4'-Methoxyphenyl)-5-octyloxypyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a flask outfitted with a reflux condenser was added 6B (300 mg), 6A (600 mg), and palladium tetrakis(triphenylphosphine) (62 mg). To this mixture was added toluene (4 ml) and a sodium carbonate solution (2M, 4.5 ml). This solution was refluxed for 16 hrs, at which time it was acidified with hydrochloric acid and extracted with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate and potassium carbonate. The solvent was removed in vacuo. The product purified by flash chromatography using 20% ethyl acetate in hexanes as the eluent to give a yellow liquid.

Aufarbeitung

  1. customTo a flask outfitted with a reflux condenser
  2. temperatureThis solution was refluxed for 16 hrs, at which time it
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate and potassium carbonate
  6. customThe solvent was removed in vacuo
  7. customThe product purified by flash chromatography
  8. customto give a yellow liquid

Quellen und Nachweise

ORD-Eintrag
ord-c2f4df1617b9419dbda3909c028e5f37
Quelldatensatz
uspto-grants-1995_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05380460

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