3-Pyridinemethanol → 1H-Imidazole-1-carboxylic acid, 3-pyridinylmethyl ester

HRID 2079246Notes

Reaction equation

HRID 2079246 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.[N:9]1([C:14](N2C=CN=C2)=[O:15])[CH:13]=[CH:12][N:11]=[CH:10]1>C(Cl)Cl>[N:9]1([C:14]([O:8][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[O:15])[CH:13]=[CH:12][N:11]=[CH:10]1

Participants

4

Reactant 2

HCID 75103-PyridinemethanolHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 104883541H-Imidazole-1-carboxylic acid, 3-pyridinylmethyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (pyridin-3-yl)methanol (2 g, 18.32 mmol) and di(1H-imidazol-1-yl)methanone (5.94 g, 36.65 mmol) in 20 mL CH2Cl2 was heated overnight at 50° C. The reaction was quenched with water, extracted twice with CH2Cl2, dried over Na2SO4, filtered, and concentrated. Purification via silica gel chromatography using 10-70% EtOAc in CH2Cl2 gave (pyridin-3-yl)methyl 1H-imidazole-1-carboxylate (3.1 g, 84%). LC/MS: m/z 204.1 (M+H)+ at 0.39 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (400 MHz, CDCl3) d 8.74 (d, J=1.9 Hz, 1H), 8.68 (dd, J=4.8, 1.4 Hz, 1H), 8.16 (s, 1H), 7.81 (m, 1H), 7.44 (s, 1H), 7.38 (m, 1H), 7.09 (s, 1H), 5.46 (s, 2H) ppm.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted twice with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-3d35fb124def480798dd97132ebbcee3
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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