4-Methoxybenzyl alcohol → 3-Benzyloxy-6-iodo-2-(4-methoxybenzyloxy)pyridine

HRID 625967

Reaktionsgleichung

Reaktionsgleichung von HRID 625967
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][OH:10])=[CH:7][CH:8]=1.[H-].[Na+].[H][H].[CH2:15]([O:22][C:23]1[C:24](Br)=[N:25][C:26]([I:29])=[CH:27][CH:28]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C.O>[CH2:15]([O:22][C:23]1[C:24]([O:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[N:25][C:26]([I:29])=[CH:27][CH:28]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

7

Edukt 4

HCID 77384-Methoxybenzyl alcoholHCID 24758Sodium hydrideHCID 110255633-(Benzyloxy)-2-bromo-6-iodopyridineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 866754893-Benzyloxy-6-iodo-2-(4-methoxybenzyloxy)pyridineAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a 0° C. solution of p-methoxybenzyl alcohol (13.83 g, 100 mmol) in 33 mL DMF was added sodium hydride (4 g, 100 mmol) slowly. The mixture was stirred at room temperature until evolution of hydrogen had ceased, and crude 3-(benzyloxy)-2-bromo-6-iodopyridine (13.01 g, 33.4 mmol) was added. The resulting solution was heated to 100° C. for 1 h under nitrogen. After cooling, the mixture was diluted with water and extracted with ethyl acetate. The aqueous layer was removed and discarded. The organic layer was collected, dried over anhydrous magnesium sulfate and purified by silica gel chromatography to afford 3-(benzyloxy)-6-iodo-2-[(4-methoxybenzyl)oxy]pyridine (12.1 g, 27.1 mmol, 81% yield). ES-MS (M+H)+=448.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. customThe aqueous layer was removed
  4. customThe organic layer was collected
  5. dry with materialdried over anhydrous magnesium sulfate
  6. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f9eb8841c74a40c78695c720eed21e84
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309199B2

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