Water → (6-Methylpyridin-3-yl)methanol

HRID 856705Notes

Reaction equation

HRID 856705 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[CH3:7][C:8]1[CH:17]=[CH:16][C:11]([C:12](OC)=[O:13])=[CH:10][N:9]=1.O.[OH-].[Na+]>C1COCC1>[CH3:7][C:8]1[N:9]=[CH:10][C:11]([CH2:12][OH:13])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 231548Methyl 6-methylnicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 11228788(6-Methylpyridin-3-yl)methanolYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To aluminum lithium hydride (2.0 g) in THF (156 ml) was added dropwise methyl 6-methylnicotinate (7.8 g) in THF (78 ml) at 0° C. The mixture was stirred for 2 hours at room temperature at 0° C., and water (7.8 ml), 15% aqueous solution of sodium hydroxide (7.8 ml), and water (23.4 ml) were sequentially added to the mixture. The mixture was filtered with Celite, and washed with methanol. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give (6-methyl-3-pyridinyl)methanol (6.3 g).

Workup

  1. filtrationThe mixture was filtered with Celite
  2. washwashed with methanol
  3. customThe solvent was removed under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0ba032bcf00e453c985b3d368b4d9380
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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