Methylparaben → Methyl 4-(pyridin-2-ylmethoxy)benzoate

HRID 1927256Notes

Reaction equation

HRID 1927256 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[CH3:9][O:10][C:11]([C:13]1[CH:14]=[CH:15][C:16](O)=[CH:17][CH:18]=1)=[O:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O.C1COCC1>[CH3:9][O:10][C:11](=[O:12])[C:13]1[CH:14]=[CH:15][C:16]([O:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 7456MethylparabenHCID 11474PiconolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylate

Product 1

HCID 2416604Methyl 4-(pyridin-2-ylmethoxy)benzoateYield 146.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of THF (50 mL) of 2-(hydroxymethyl)pyridine (1.5 g), methyl p-hydroxybenzoate (2.1 g), and triphenylphosphine (5.0 g) was added diisopropyl azodicarboxylate (3.9 g) at 0° C., which was stirred for 20 minutes at room temperature. Water was added to the reaction solution, which was extracted with ethyl acetate. The solvent was evaporated from the organic layer under a reduced pressure, and the residue was purified by NH silica gel chromatography (heptane:ethyl acetate=2:1), then purified by silica gel chromatography (heptane:ethyl acetate=1:1) to obtain the titled compound (4.9 g).

Workup

  1. extractionwas extracted with ethyl acetate
  2. customThe solvent was evaporated from the organic layer under a reduced pressure
  3. customthe residue was purified by NH silica gel chromatography (heptane:ethyl acetate=2:1)
  4. custompurified by silica gel chromatography (heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-a0f304c752a7430385d0618503412e29
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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