4-Nitrobenzaldehyde → (3-Methoxymethoxypyridin-2-yl)-(4-nitrophenyl)methanol

HRID 2228185Notes

Reaction equation

HRID 2228185 reaction equation
Br[C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[Li].[N+:18]([C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=1)([O-:20])=[O:19]>C(OCC)C.CCCCCC.O1CCCC1.O>[CH3:11][O:10][CH2:9][O:8][C:7]1[C:2]([CH:25]([C:24]2[CH:23]=[CH:22][C:21]([N+:18]([O-:20])=[O:19])=[CH:28][CH:27]=2)[OH:26])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

9

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 3028194Lithium2×HCID 115865732-Bromo-3-(methoxymethoxy)pyridineHCID 178418339Butyllithium

Product 1

HCID 18472436(3-Methoxymethoxypyridin-2-yl)-(4-nitrophenyl)methanolYield 88.5%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

Under nitrogen atmosphere, to a solution of 2-bromo-3-methoxymethoxypyridine (10.00 g) in diethylether (150 ml) was added a solution of n-butyllithium in hexane (1.6M, 31.5 ml) at −78° C., and the mixture was stirred for 1 hour to prepare the lithium salt. The resulting lithium salt was dropwise added to a solution of 4-nitrobenzaldehyde (6.93 g) in tetrahydrofuran (100 ml) cooled at −78° C., and the mixture was stirred at the same temperature for 3 hours. To the reaction mixture was added water to stop the reaction, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1:3→1:2) to give (3-methoxymethoxypyridin-2-yl)—(4-nitrophenyl)-methanol (11.78 g) as yellow oil.

Workup

  1. stirringthe mixture was stirred at the same temperature for 3 hours
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium chloride solution
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was separated
  8. custompurified with column chromatography (ethyl acetate/hexane=1:3→1:2)

Sources & evidence

ORD record
ord-7db39247387746ba8d1be423be2905e2
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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