2,2-Dimethylbutanol → 6-Phenoxy-2-pyridylmethyl 2,2-dimethylbutyl ether

HRID 2371470Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2371470
[OH-].[Na+].[CH3:3][C:4]([CH3:9])([CH2:7][CH3:8])[CH2:5][OH:6].Cl[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:13]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:3][C:4]([CH3:9])([CH2:7][CH3:8])[CH2:5][O:6][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:13]=1

Komponenten

6

Edukt 3

HCID 144542,2-DimethylbutanolHCID 14798Sodium HydroxideHCID 138492412-Chloromethyl-6-phenoxypyridine

Produkt 1

HCID 148789686-Phenoxy-2-pyridylmethyl 2,2-dimethylbutyl etherAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

4.4 Grams of a 45% aqueous sodium hydroxide solution, 100 mg of tetrabutylammonium bromide and 5 ml of toluene were mixed, and to the resulting mixture, a solution of 0.7 g of 2,2-dimethylbutanol and 1.72 g of 2-chloromethyl-6-phenoxypyridine in 10 ml of toluene was added at room temperature under a nitrogen atmosphere. After 12 hours, the reaction solution was poured into 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. The solvent was removed under reduced pressure, and the residue was treated by preparative thin layer chromatography (developing solvent, hexane:ethyl acetate=5:1) to obtain 0.45 g of desired 6-phenoxy-2-pyridylmethyl 2,2-dimethylbutyl ether [present compound (17)] as an oily product.

Aufarbeitung

  1. extractionextracted twice with diethyl ether
  2. washwashed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. additionthe residue was treated by preparative thin layer chromatography (developing solvent, hexane:ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-d138186232704f38b3b30e69e9b9f1ef
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05093373

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