2-Acetylpyridine → alpha-Methyl-2-pyridinemethanol

HRID 555786Notes

Reaction equation

HRID 555786 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH:1]([OH:3])[CH3:2]

Participants

4

Reactant 2

HCID 142862-AcetylpyridineHCID 4311764Sodium borohydride

Product 1

HCID 86784alpha-Methyl-2-pyridinemethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-Acetyl-pyridine (2.0 g, 16.5 mmol) in MeOH (33 mL) is treated by NaBH4 (624 mg, 16.5 mmol) at 0° C. After completion, the reaction mixture is quenched by H2O, EtOAc is added and the organic layer is washed with brine, dried over MgSO4 and evaporated in vacuo to provide crude product, which is submitted to the next step without further purification; ES-MS: M+=124.0; 1HNMR(DMSO-d6) 8.45 (d, 1H), 7.75 (td, 1H), 7.50 (d, 1H), 7.20 (dd, 1H), 5.30 (d, 1H), 4.70-4.60 (m, 1H), 1.30 (d, 3H).

Workup

  1. customAfter completion, the reaction mixture is quenched by H2O, EtOAc
  2. additionis added
  3. washthe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customto provide crude product, which
  7. customis submitted to the next step without further purification

Sources & evidence

ORD record
ord-5229a66479a34240a9bfad21b6f4fcc6
Source dataset
uspto-grants-2011_11
Patent number
US08053457B2

Reaction notes

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