Sodium sulfate decahydrate → (2-Ethyl-6-methylpyridin-3-yl)methanol

HRID 591493Notes

Reaction equation

HRID 591493 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1[N:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:10]=1[C:11](OC)=[O:12])[CH3:8].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH2:7]([C:9]1[C:10]([CH2:11][OH:12])=[CH:15][CH:16]=[C:17]([CH3:19])[N:18]=1)[CH3:8]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 57561949Methyl 2-ethyl-6-methylnicotinate

Product 1

HCID 89768184(2-Ethyl-6-methylpyridin-3-yl)methanolYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of lithium aluminum hydride (220 mg) and THF (dry) (15 mL) was added a solution of methyl 2-ethyl-6-methylnicotinate (519 mg) in THF (dry) (5 mL) at 0° C. The mixture was stirred at 0° C. under nitrogen atmosphere for 20 min. To the mixture was added sodium sulfate decahydrate (1.8 g) and the mixture was stirred overnight. After filtrating, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (365 mg).

Workup

  1. stirringthe mixture was stirred overnight
  2. filtrationAfter filtrating
  3. concentrationthe filtrate was concentrated in vacuo
  4. customthe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-434869779f524443a9e33664818676e2
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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