2-Methylnicotinic acid → (2-Methylpyridin-3-yl)methanol

HRID 7168

Reaction equation

HRID 7168 reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].B.C1COCC1>CO>[CH3:1][C:2]1[C:3]([CH2:4][OH:5])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 6433732-Methylnicotinic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 302564(2-Methylpyridin-3-yl)methanolYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To 2-Methylnicotinic acid (1.00 g, 7.29 mmol) was added BH3.THF (1.0 m in THF, 18 mL, 18 mmol) and the resultant mixture was heated to 80° C. for 20 hours. MeOH (6 mL) was added and the mixture was heated to 80° C. for an additional 2 hours before being cooled to room temperature and concentrated under reduced pressure. The resultant crude syrup was repeatedly dissolved in MeOH (5 mL) and concentrated (3×). Purification by column chromatography on silica gel (4:1—EtOAc:Hexanes) afforded the desired alcohol (700 mg, 80%) as a white solid. 1H NMR (CDCl3) δ 1.96 (t, 1H, J=5.4 Hz), 2.73 (s, 3H), 4.81 (d, 2H, J=5.4 Hz), 7.32 (dd, 1H, J=7.8, 6.3 Hz), 8.03 (d, 1H, J=7.8 Hz), 8.73 (d, 1H, J=5.7 Hz).

Workup

  1. temperaturebefore being cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resultant crude syrup was repeatedly dissolved in MeOH (5 mL)
  4. concentrationconcentrated (3×)
  5. customPurification by column chromatography on silica gel (4:1—EtOAc:Hexanes)

Sources & evidence

ORD record
ord-6e8c842ed3224a8bbc5a5afdb8fca125
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Linked notes

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