Benzyl Alcohol → HCID 66607413, compound

HRID 1625858Notes

Reaction equation

HRID 1625858 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:12]=[N:13][C:14](Cl)=[CH:15][CH:16]=2)=[O:10])=[CH:5][CH:4]=1)[CH3:2].[CH2:18]([OH:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[H-].[Na+].O>CN1CCCC1=O>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:12]=[N:13][C:14]([O:25][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:16]=2)=[O:10])=[CH:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 49762710HCID 49762710, compound

Product 1

HCID 66607413HCID 66607413, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The above 6-chloro-3-pyridyl 4-ethylphenyl ketone (1.68 g) was dissolved in N-methyl-2-pyrrolidinone (20 ml), and thereto were added benzylalcohol (815 ml) and 60% sodium hydride (275 mg). The mixture was stirred at room temperature for 6 hours, and then at 90° C. for one hour. The reaction mixture was cooled to room temperature, and water was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with water and subsequently with brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-95:5) to give 6-benzyloxy-3-pyridyl 4-ethylphenyl ketone (1.68 g) as colorless oil. APCI-Mass m/Z 318 (M+H).

Workup

  1. waitat 90° C. for one hour
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and subsequently with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-95:5)

Sources & evidence

ORD record
ord-c896eb8101a14a45a5f2697e7d3298f0
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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