Methanol → (2-Methoxypyridin-3-yl)methanol

HRID 1972650Notes

Reaction equation

HRID 1972650 reaction equation
[CH3:1][O:2][C:3]1[N:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](O)=[O:6].CO>O1CCCC1>[CH3:1][O:2][C:3]1[C:4]([CH2:5][OH:6])=[CH:8][CH:9]=[CH:10][N:11]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 7080932-Methoxynicotinic acid

Product 1

HCID 10630565(2-Methoxypyridin-3-yl)methanolYield 83.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a 100-mL round-bottomed flask was added 2-methoxynicotinic acid (1.52 g, 9.93 mmol, Aldrich, St. Louis, Mo.) and borane methyl sulfide complex (3.77 mL, 39.7 mmol, Aldrich, St. Louis, Mo.) in tetrahydrofuran (30 mL). The reaction mixture was stirred at 70° C. for 16 h. The mixture was cooled to 0° C. and MeOH (10 mL) was added dropwise. After the addition was completed, the reaction mixture was stirred for further 20 min. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 60% EtOAc/hexanes to give (2-methoxy-3-pyridinyl)methanol (1.15 g) as a white solid.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. additionAfter the addition
  3. stirringthe reaction mixture was stirred for further 20 min
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by silica gel chromatography
  6. washeluting with 60% EtOAc/hexanes

Sources & evidence

ORD record
ord-1c9a8706e86f4770834a9bca14624957
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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