Potassium Sodium Tartrate → (6-Methoxypyridin-2-yl)methanol

HRID 706656Notes

Reaction equation

HRID 706656 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9](O)=[O:10])[CH:6]=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCCC1>[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 5708916-Methoxypicolinic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 12325389(6-Methoxypyridin-2-yl)methanolYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A cold solution of 6-methoxypicolinic acid (1.8 g, 11.8 mmol) in tetrahydrofuran (0.3M, 40 mL) was treated with lithium aluminum hydride (11.8 mL, 11.8 mmol) at 0° C. This mixture was stirred at 0° C. for 30 minutes, poured into a beaker containing aqueous saturated Rochelle's salt and stirring at ambient temperature continued for 1 hour. The product was extracted from EtOAc, dried (phase separator silicone treated filter paper) paper, concentrated (1.13 g, 69% yield) as a clear oil.

Workup

  1. additionpoured into a beaker
  2. stirringstirring at ambient temperature
  3. waitcontinued for 1 hour
  4. extractionThe product was extracted from EtOAc
  5. customdried
  6. addition(phase separator silicone treated filter paper) paper
  7. concentrationconcentrated (1.13 g, 69% yield) as a clear oil

Sources & evidence

ORD record
ord-84c9fcb29d4d479ca3e9840ff1274690
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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