Sodium Hydroxide → 6-Phenoxy-2-pyridylmethyl 2-ethyl-2-methylbutyl ether

HRID 1084773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1084773
[OH-].[Na+].[CH2:3]([C:5]([CH3:10])([CH2:8][CH3:9])[CH2:6][OH:7])[CH3:4].[O:11]([C:18]1[N:23]=[C:22]([CH2:24]Cl)[CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:3]([C:5]([CH3:10])([CH2:8][CH3:9])[CH2:6][O:7][CH2:24][C:22]1[CH:21]=[CH:20][CH:19]=[C:18]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:23]=1)[CH3:4]

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 876052,2-Diethyl-1-propanolHCID 138492412-Chloromethyl-6-phenoxypyridine

Produkt 1

HCID 148790006-Phenoxy-2-pyridylmethyl 2-ethyl-2-methylbutyl etherAusbeute 71,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

Under a nitrogen atmosphere, 3.83 g of a 45% aqueous sodium hydroxide solution, 120 mg of tetrabutylammonium bromide and 5 ml of toluene were mixed, and to the resulting mixture solution, a solution of 1.0 g of 2-ethyl-2-methylbutanol and 1.51 g of 6-phenoxy-2-chloromethylpyridine in 5 ml of toluene was added at room temperature. After stirring at room temperature for 16 hours, the reaction solution was poured into dilute hydrochloric acid-ice water and extracted twice with toluene. The toluene 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, n-hexane: ethyl acetate=50:1) to obtain 1.48 g of desired 6-phenoxy-2-pyridylmethyl 2-ethyl-2-methylbutyl ether [present compound (35)] as a colorless oily product.

Aufarbeitung

  1. extractionextracted twice with toluene
  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

Quellen und Nachweise

ORD-Eintrag
ord-1b780f3b456c487b80e83376170b96df
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05006538

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