Sodium sulfate decahydrate → HCID 22678477, compound

HRID 79273Notes

Reaction equation

HRID 79273 reaction equation
[CH3:1][O:2][C:3]1[N:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:4]=1[C:5](OC)=[O:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[C:4]([CH2:5][OH:6])=[CH:9][CH:10]=[C:11]([CH3:13])[N:12]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 10910170METHYL 2-METHOXY-6-METHYLPYRIDINE-3-CARBOXYLATEHCID 21226445Aluminium lithium hydride

Product 1

HCID 22678477HCID 22678477, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of methyl 2-methoxy-6-methylnicotinate (5.60 g, 30.9 mmol) in dry tetrahydrofuran (155 mL, 30.9 mmol) under an atmosphere of nitrogen was cooled in an ice bath. Lithium aluminum hydride (1.23 g, 30.9 mmol) was added as a slurry in tetrahydrofuran and the mixture was stirred with cooling in an ice bath for 75 minutes. The reaction mixture was diluted with tetrahydrofuran (30 mL). Some Celite® was added followed by sodium sulfate decahydrate to quench. The mixture was filtered and concentrated under vacuum to give (2-methoxy-6-methylpyridin-3-yl)methanol (4.7 g) which was used without purification.

Workup

  1. temperaturewith cooling in an ice bath for 75 minutes
  2. additionSome Celite® was added
  3. customto quench
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8705ef42abdc4b419469809d7be231d6
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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