Methyl 6-methylnicotinate → (6-Methylpyridin-3-yl)methanol

HRID 706647Notes

Reaction equation

HRID 706647 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][N:3]=1.[BH4-].[Na+]>CO>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([CH2:6][OH:7])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 231548Methyl 6-methylnicotinateHCID 4311764Sodium borohydride

Product 1

HCID 11228788(6-Methylpyridin-3-yl)methanolYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 6-methylnicotinate (16.3 g, 108 mmol) in MeOH (150 mL) was treated with sodium borohydride (12.2 g, 323 mmol) at ambient temperature in portions. The mixture was quenched with water (100 mL) and concentrated. This mixture was diluted with water (300 mL) and extracted with EtOAc. The combined organic extracts were dried (phase separator silicone treated filter paper) and concentrated to give (6-methylpyridin-3-yl)methanol (8.5 g, 64% yield) as a light yellow oil.

Workup

  1. customThe mixture was quenched with water (100 mL)
  2. concentrationconcentrated
  3. additionThis mixture was diluted with water (300 mL)
  4. extractionextracted with EtOAc
  5. customThe combined organic extracts were dried
  6. addition(phase separator silicone treated filter paper)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-56f6f8d3f0f84a068123bd9030f0f0e8
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

Loading…