Phenol → HCID 58483799, compound

HRID 1948224Notes

Reaction equation

HRID 1948224 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O.[CH3:39][O:40][C:41]1[N:46]=[CH:45][C:44]([CH2:47]O)=[CH:43][CH:42]=1>C1COCC1>[CH3:39][O:40][C:41]1[CH:42]=[CH:43][C:44]([CH2:47][O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:45][N:46]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 12259941(6-Methoxypyridin-3-yl)methanol

Product 1

HCID 58483799HCID 58483799, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to Scheme 16 Method A: Phenol (1.5 eq, 2.80 mmol, 0.26 g), PPh3 (2 eq, 3.70 mmol, 1.20 g) and DEAD (2 eq, 3.70 mmol, 1.60 g) were added to a solution of (6-methoxypyridin-3-yl)methanol (1 eq, 1.87 mmol, 0.26 g) in THF (6 mL). The reaction mixture was stirred overnight at room temperature. After evaporation of the solvent, the reaction mixture was diluted with water. The organic layer washed with saturated NaHCO3 solution, dried over Na2SO4, filtered and evaporated. The resulting crude residue was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2) using cyclohexane/AcOEt 85/15 to afford 2-methoxy-5-(phenoxymethyl)pyridine (0.93 mmol, 0.20 g, 49%) as a pale oil.

Workup

  1. customAfter evaporation of the solvent
  2. additionthe reaction mixture was diluted with water
  3. washThe organic layer washed with saturated NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting crude residue was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2)

Sources & evidence

ORD record
ord-53d095c068b841678b4ed21e872adb1a
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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