Borane;tetrahydrofuran → (3-Ethoxypyridin-2-yl)methanol

HRID 7151

Reaction equation

HRID 7151 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([C:10](O)=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:2].B.C1COCC1>C1COCC1>[CH2:1]([O:3][C:4]1[C:5]([CH2:10][OH:11])=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 213332043-Ethoxypyridine-2-carboxylic acid

Product 1

HCID 22018715(3-Ethoxypyridin-2-yl)methanolYield 124.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-ethoxypicolinic acid (0.202 g, 1.21 mmol) in dry THF (1 mL) was added BH3.THF (1.0 M in THF, 5.0 mL, 5.0 mmol) and the reaction mixture stirred at room temperature for 2.5 hours. The mixture was then quenched with methanol (20 mL), stirred at reflux for 4 hours and concentrated under reduced pressure. The resultant crude product was dissolved in methanol (3×15 mL) and concentrated to give the desired crude alcohol (0.231 g) as an orange solid. 1H NMR (CDCl3): δ 1.46 (t, 3H, J=7.0 Hz), 4.07 (q, 2H, J=7.0 Hz), 4.74 (s, 2H), 7.09–7.20 (m, 2H), 8.14 (d, 1H, J=4.5 Hz).

Workup

  1. customThe mixture was then quenched with methanol (20 mL)
  2. stirringstirred
  3. temperatureat reflux for 4 hours
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe resultant crude product was dissolved in methanol (3×15 mL)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ccee693cbf364a5ab48c75de7b438da3
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Linked notes

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