Hydrochloric Acid → (3-Ethoxy-4-nitrophenyl)(2-pyridyl)methanol

HRID 856744Notes

Reaction equation

HRID 856744 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([O:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[CH:14]=[O:15])[CH3:9].O.Cl>CCOCC.C([Li])CCC.C1COCC1>[CH2:8]([O:10][C:11]1[CH:12]=[C:13]([CH:14]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[OH:15])[CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[CH3:9]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 79732-BromopyridineHCID 22038897HCID 22038897, compound

Product 1

HCID 22938745(3-Ethoxy-4-nitrophenyl)(2-pyridyl)methanolYield 49%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolventHCID 178418339ButyllithiumSolvent

Procedure

To a solution of 2-bromopyridine (4.0 g) in dry ether (50 ml), n-butyl lithium (19.2 ml, 1.6M hexane solution) was added dropwise under argon atmosphere at −78° C. After finishing the dropping, the mixture was stirred for 1 hour, and a solution of 3-ethoxy-4-nitrobenzaldehyde (5.0 g) in dry ether (100 ml) and dry THF (50 ml) was added dropwise to the mixture. After finishing the dropping, and the mixture was allowed to be at room temperature and the mixture was stirred overnight. Water was added to the mixture, the mixture was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate), to give (3-ethoxy-4-nitrophenyl)(2-pyridyl)methanol (3.4 g) as dark brown oil.

Workup

  1. customto be at room temperature
  2. stirringthe mixture was stirred overnight
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-e7e3844cdedc449d8af0b2d50c68537b
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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