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

HRID 1084773Notes

Reaction equation

HRID 1084773 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 148790006-Phenoxy-2-pyridylmethyl 2-ethyl-2-methylbutyl etherYield 71.9%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1b780f3b456c487b80e83376170b96df
Source dataset
uspto-grants-1991_04
Patent number
US05006538

Reaction notes

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