Sodium hydride → HCID 14878964, Verbindung

HRID 2371469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2371469
[H-].[Na+].Cl[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:6]=1.[Cl:18][CH2:19][C:20]([CH3:24])([CH3:23])[CH2:21][OH:22]>CN(C=O)C>[Cl:18][CH2:19][C:20]([CH3:24])([CH3:23])[CH2:21][O:22][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:6]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 834071-Propanol, 3-chloro-2,2-dimethyl-HCID 138492412-Chloromethyl-6-phenoxypyridine

Produkt 1

HCID 14878964HCID 14878964, VerbindungAusbeute 11,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Under a nitrogen atmosphere, 0.65 g of sodium hydride (60% oily suspension) was suspended in 10 ml of dry DMF, and a solution of 3.23 g of 2-chloromethyl-6-phenoxypyridine and 2.00 g of 3-chloro-2,2-dimethylpropanol in 10 ml of dry DMF was added dropwise with ice-cooling. After stirring for 12 hours at room temperature, the reaction solution was poured into dilute hydrochloric acid-ice water and extracted twice with diethyl ether. The ether layers were combined, washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was subjected to column chromatography on silica gel (developing solvent, hexane:ethyl acetate=50:1) to obtain 0.52 g of desired 6-phenoxy-2-pyridylmethyl 3-chloro-2,2-dimethylpropyl ether [present compound (1)] as a colorless oily product.

Aufarbeitung

  1. temperaturecooling
  2. extractionextracted twice with diethyl ether
  3. washwashed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-af0a3eec97c943dd923387a345627617
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05093373

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