Benzyl Alcohol → HCID 23103626, compound

HRID 2116505Notes

Reaction equation

HRID 2116505 reaction equation
Cl[C:2]1[C:7]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=2)O)=[N:6][CH:5]=[CH:4][N:3]=1.[OH-].[K+].C([O-])([O-])=O.[K+].[K+].[CH2:26]([OH:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.COCCOCCN(CCOCCOC)CCOCCOC>C1(C)C=CC=CC=1.O>[CH2:26]([O:33][C:2]1[C:7]([CH2:8][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=2)=[N:6][CH:5]=[CH:4][N:3]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 5

HCID 244Benzyl AlcoholHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 23103646HCID 23103646, compound

Product 1

HCID 23103626HCID 23103626, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Next, to a solution of (2-chloropyrazin-3-yl)-(4-ethylphenyl)methanol (3.1 g, 0.0125 mol) in toluene (24 mL), KOH (2.8 g, 0.050 mol), K2CO3 (1.7 g, 0.0125 mol), benzyl alcohol (1.89 g, 0.0175 mol) and tris[2-(2-methoxyethoxy)ethyl]amine (0.40 g, 0.00125 mol) were added and stirred at 120° C. for 2 hours. After cooling the reaction mixture to room temperature, water was poured and the resulting mixture was extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=87:13) to give 2-benzyloxy-3-(4-ethylbenzyl)pyrazine (420 mg, 11%) as a yellow oil.

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. extractionthe resulting mixture was extracted twice with ethyl acetate
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=87:13)

Sources & evidence

ORD record
ord-6267770f24204e0a98d9ccf86a5691d0
Source dataset
uspto-grants-2008_10
Patent number
US07439232B2

Reaction notes

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